ライフサイエンスコーパス: oxazoline

1 a key cyclopentenone harboring a spirocyclic oxazoline.

2 e to 4-(methoxycarbonyl)-5,5-disubstituted 2-oxazoline.

3 wer GB (321 kJ/mol less) than 2,4-dimethyl-3-oxazoline.

4 cNAc-Fc homodimer) with the synthetic glycan oxazolines.

5 rther reaction with an amine base provides 2-oxazolines.

6 cooperative effects in meta-substituted aryl oxazolines.

7 nsation of isocyanides and aldehydes to form oxazolines.

8 were prepared by cationic polymerization of oxazolines.

9 ivity between the t-Bu- and i-Pr-substituted oxazolines.

10 Cyclohexylamino oxazoline 1 (AGN 190837), an analogue of 2 (Bay a6781),

11 tereospecifically and regiospecifically into oxazolines (+/-)-13 and (+/-)-14 and into cyclic carbama

12 ycosides having a cis-1,2-fused pyranose-1,3-oxazoline-2-thione structure and bearing different subst

13 Non-C(2) symmetric oxazolines (20-25) have also been examined as ligands, a

14 ide 24b via electrocyclic ring opening of an oxazoline 23b.

15 1 (X = CH(2)), imidazoline 2 (X = NH), and 2-oxazoline 3 (X = O).

16 Novel intermediate oxazoline[3,2-a]pyridiniums were facilely prepared from

17 C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidativ

18 presence of SOCl(2) produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted thiaz

19 Chiral and achiral 3-methoxynaphthalen-2-yl oxazolines 4a,b failed to undergo an aromatic nucleophil

20 e2)2 (M = Ti, Zr, Hf; Ox(R) = 4,4-dimethyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-ter

21 hyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperatur

22 With use of this method chiral oxazoline 6, bisoxazoline 7, bisthiazoline 8, and 5,6-di

23 , the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7).

24 forming the salt of 2,4,4,5,5-pentamethyl-2-oxazoline (8) with loss of thianthrene (Th).

25 reaction was employed to construct a chiral oxazoline 9 (99% yield, 98% ee) that served the dual pur

26 s diacylated product undergoes a second aryl oxazoline acylation on its remaining secondary amine, al

27 drogenations mediated by the chiral, carbene-oxazoline analogue of Crabtree's catalyst "cat" in asymm

28 ns, together with the previously constructed oxazoline analogues 5d and 6d, were subjected to biologi

29 ansformation may be achieved by oxidation of oxazoline analogues of phenolic and indolic amides.

30 and instead proceeds through arabinose amino-oxazoline and anhydronucleoside intermediates.

31 ed by chemical synthesis of a large N-glycan oxazoline and its subsequent enzymatic ligation to GlcNA

32 olytic activity toward both the Man(9)GlcNAc oxazoline and the product as well as to its enhanced act

33 stereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers.

34 ition states with t-Bu- and i-Pr-substituted oxazolines and suggested a possible explanation for the

35 f N-acylbenzotriazoles in the preparation of oxazolines and thiazolines under mild conditions and sho

36 catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline 4-carboxylate to a nitroalke

37 However, oxazoline anion 30, a synthetic equivalent of ethyl phen

38 )(NAr)(hoz)2+] (hoz = 2-(2'-hydroxyphenyl)-2-oxazoline) (Ar = 2,4,6,-(Me)C(6)H(2); 4-(OMe)C(6)H(4); 4

39 Third, readily available bis(oxazolines) are shown for the first time to be effective

40 utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand.

41 rected] could not take more complex N-glycan oxazoline as substrate for transglycosylation, indicatin

42 esses transglycosylation activity with sugar oxazoline as the donor substrate, but the transglycosyla

43 ) core by use of azido-containing Man3GlcNAc oxazoline as the donor substrate.

44 ted substituents on the aromatic ring and an oxazoline as the heterocyclic moiety, demonstrated in vi

45 f the chemical synthesis of defined N-glycan oxazolines as donor substrates, the expression of the Fc

46 can still catalyse synthetic processes using oxazolines as donors, but which do not hydrolyse the rea

47 ynthesis of bespoke N-glycans using N-glycan oxazolines as glycosyl donors.

48 able to use both bi- and triantennary glycan oxazolines as substrates for transglycosylation, in cont

49 se-catalyzed transglycosylation, using sugar oxazolines as the donor substrates.

50 protophormiae (Endo-A) with synthetic sugar oxazolines as the donor substrates.

51 The studies performed with chiral oxazolines as vehicles for a number of C-C bond-forming

52 y diastereoselective allylation, and a novel oxazoline-assisted piperidinone forming reaction to prov

53 yl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperature and below, affording five

54 nd their derivatives, including ortho ester, oxazoline, azido epoxide, as well as sulfonamide-, amide

55 Reported here is the use of an oxazoline-based directing group capable of overriding th

56 pha,omega-hydroxy-end-capped poly(2-methyl-2-oxazoline)-block-poly(dimethylsiloxane)-block-poly(2-met

57 By chemical modification of the oxazoline, both the gamma-lactone (28) and the delta-lac

58 did not recognize the complex-type N-glycan oxazoline but could efficiently use the high-mannose-typ

59 This enzyme-bound aryl oxazoline can be transferred by VibF to various amine ac

60 etylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamid

61 stablish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantio

62 zoic acid salts of the chiral copper(II) bis(oxazoline) catalyst deliver both diastereomers of the He

63 secondary benzyl chlorides with a Ni(II)/bis(oxazoline) catalyst in the presence of Mn(0) as a stoich

64 ylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-couplin

65 can be achieved with the aid of a nickel/bis(oxazoline) catalyst.

66 the stereochemical outcome of the copper-bis(oxazoline)-catalyzed C-H insertion reaction between meth

67 son, a 1:1 mixture of the palladium pyridine-oxazoline complex (N-N)Pd(Me)Cl inverted question markN-

68 An iridium carbene oxazoline complex was used to catalyze hydrogenations of

69 A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in p

70 ridines is catalyzed by a novel iron(II) bis(oxazoline) complex.

71 genation mixtures formed using these iridium-oxazoline complexes.

72 A family of bis(oxazoline) complexes of coordinatively unsaturated monom

73 simple catalytic hydrogenation at C-1 of an oxazoline constructed from the corresponding 2-aminopyra

74 , the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration

75 This strategy is based on chiral bis(oxazoline) copper(II) complex-catalyzed enantioselective

76 the outer mannose residues of the Man3GlcNAc-oxazoline core, thus allowing introduction of large olig

77 The oligosaccharide oxazoline corresponding to the biantennary complex-type

78 exo-Diels-Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the

79 do selectivity enhancements delivered by bis(oxazoline)-Cu(II) Lewis acid catalysts in the Diels-Alde

80 t, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst c

81 stereoselectivity (>99:1 dr) observed in the oxazoline-directed, Pd(II)-catalyzed sp(3) C-H bond iodi

82 e peptide precursor from the oligosaccharide oxazoline donor substrates.

83 lipid A region-was synthesized using an 1,3-oxazoline donor, which was followed by coupling with an

84 thesis by transglycosylation using activated oxazoline donors.

85 the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and

86 ne-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the

87 efficiently use the high-mannose-type glycan oxazoline for transglycosylation.

88 rolytic activity but are able to take glycan oxazolines for transglycosylation.

89 the epoxides were converted directly to the oxazoline form of the target molecules using a Ritter re

90 results show that controlling the balance of oxazoline formation and glycosylation is key to achievin

91 4-carboxy-VibF in the first demonstration of oxazoline formation by an NRPS cyclization domain.

92 Highly selective cis-oxazoline formation is achieved starting from anti-E-bis

93 no impact on the diastereoselectivity of the oxazoline formation, and chiral triazolylidenes did not

94 A powerful method for the synthesis of 2-oxazolines from silyl-protected beta-hydroxyamides is re

95 The formation of chiral oxazolines from these materials provided interesting and

96 lyzed by [Cu{(S,S)-tBu-box}](SbF6)2 [box=bis(oxazoline)] generate chiral alpha-functionalized alpha-h

97 stituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcP

98 The use of N-glycan oxazolines, high energy intermediates on the hydrolytic

99 Using our method, oxazoline hydroxamates with diverse 2-substituents were

100 hydes, imines, and activated olefins to form oxazolines, imidazolines, and pyrrolines, respectively.

101 ene ortho C-H bonds with pyridine, pyrazole, oxazoline, imine, urea, amide...

102 e converted into 2-(9'-fluorenylmethyloxy)-2-oxazoline in high yield, thereby providing a new pathway

103 oxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ,

104 in situ deprotected and dehydrated to give 2-oxazolines in good yields.

105 cient to take various modified N-glycan core oxazolines, including the bisecting sugar-containing der

106 Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-posi

107 Oxazolines incorporating a hydroxamic acid, which is bel

108 yanide-induced ylide generation via a labile oxazoline intermediate (62 to 66).

109 ition, and electrocyclic ring opening of a 4-oxazoline intermediate affords the indoloquinone 31 in a

110 structural and electronic properties of the oxazoline intermediate are similar to the known chitinas

111 s double displacement mechanism involving an oxazoline intermediate distinguishes the family 18 chiti

112 tly observe both a Michaelis complex and the oxazoline intermediate.

113 the catalytic acid/base for reaction via an oxazoline intermediate.

114 midins act as transition state analogs of an oxazoline intermediate.

115 d two potential hydrolysis intermediates (an oxazoline ion and an oxocarbenium ion) to a family 19 ba

116 hevamine (a family 18 chitinase) involves an oxazoline ion intermediate stabilized by the neighboring

117 sugar D, thus preventing the formation of an oxazoline ion intermediate.

118 Structural and electronic features of the oxazoline ion likely to be important in the design of ne

119 omers (2-vinylpridine (2VP), 2-isopropenyl-2-oxazoline (IPOx)).

120 ral 2,2'-(2,6-pyridinediyl)bis(4-isopropyl-2-oxazoline) (iPr-Pybox) to a self-assembled Co(II)-[W(V)(

121 mistry of the stereogenic carbon next to the oxazoline is not necessarily the dominant chiral center

122 led that C(4)-phenyl substitution on the bis(oxazoline) is optimal for high asymmetric induction.

123 eed upon to be caused by an intermediate 1,2-oxazoline, is often bypassed by introducing extra synthe

124 f the substituents on the aryl moiety of the oxazoline lead to a surprising modulation of reactivity.

125 pper triflate (CuOTf) and a C2-symmetric bis-oxazoline ligand (5a-c).

126 ew, readily available bidentate isoquinoline-oxazoline ligand furnishes excellent ee's and good yield

127 the electronically asymmetric quinoline and oxazoline ligand modules.

128 Using a new chiral pyridine oxazoline ligand, good to high enantioselectivity is ach

129 reocenters is disclosed using a new pyridine oxazoline ligand.

130 reocenters was developed using a new pyridyl-oxazoline ligand.

131 By using a bis(oxazoline) ligand, good yields and enantioselectivities

132 opper(I) catalyst equipped with a chiral bis(oxazoline) ligand, high yields and enantioselectivities

133 tioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselect

134 dium complexes of the N-heterocyclic carbene oxazoline ligands 1 in asymmetric hydrogenations of aryl

135 a range of novel gem-disubstituted ferrocene-oxazoline ligands and their application in both the asym

136 A series of phosphine-oxazoline ligands based on proline are reported.

137 llylation under NHK conditions using modular oxazoline ligands developed in our laboratory.

138 ear to differ from the traditional phosphine-oxazoline ligands in that the stereochemistry of the ste

139 -disubstitution of i-Pr-containing ferrocene oxazoline ligands results in increased enantioselectivit

140 design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopro

141 Air-stable P-chiral dihydrobenzooxaphosphole oxazoline ligands were designed and synthesized.

142 me using chiral acetyl-protected aminomethyl oxazoline ligands.

143 on a set of newly developed chiral quinolyl oxazoline ligands.

144 A series of eight novel bis(oxazoline) ligands incorporating gem-disubstitution on o

145 A screening study of bis(oxazoline) ligands reveals that aryl stereodirecting gro

146 mmercially available or readily prepared bis(oxazoline) ligands such as (4R,5S)-Ph(2)BoxH, (4S,5R)-Ar

147 Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept

148 o acids, bioactive molecules, and chiral bis(oxazoline) ligands.

149 mpounds is disclosed using a chiral pyridine oxazoline-ligated palladium catalyst under mild conditio

150 nce by the sugar acetamido moiety to form an oxazoline-like intermediate.

151 -Me(2)Box]La[N(TMS)(2)](2) (Box = 2,2'-bis(2-oxazoline)methylenyl; Ar = 4-tert-butylphenyl, 1-naphthy

152 Employing just 4 mol % bis(oxazoline)-Mg(OTf)(2) complex with an amine cocatalyst,

153 in the stereochemistry of their butyrate or oxazoline moieties were not recognized by human T cells.

154 n the substitution pattern on the oxazole or oxazoline moieties, mono- and dioxabacteriochlorins may

155 ique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to

156 nd synthesized by cationic polymerization of oxazolines on mesoporous silica.

157 eptides capped with an N-terminal 2-alkoxy-2-oxazoline or 2-oxazolidinone unit.

158 ckbone carbonyl carbon to form a thiazoline, oxazoline, or methyloxazoline ring.

159 er both in substrate and the [Cu(R,R)-Ph-bis(oxazoline)]OTf(2) catalyst and zero order in TEMPO.

160 y, where the stereogenic center alpha to the oxazoline oxygen atom is significant.

161 Cobalt oxazoline palladacycles (COP) containing acetylacetonate

162 Cobalt oxazoline palladacyclic (COP) complex 4 containing aceta

163 ly(vinylpyrrolidone)), PMOX (poly(2-methyl-2-oxazoline)), PDMA (poly(N,N-dimethyl acrylamide)), and P

164 rther neutral polymer, namely poly(2-ethyl-2-oxazoline) (PEOz) can be successfully used as a dipole l

165 indirectly attributed to interaction of the oxazoline-phenyl substituent with the palladium and with

166 r and demonstrate that the threonine-derived oxazoline plays a critical role in determining the kinet

167 m and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter w

168 Smart poly(2-oxazoline) (POx)-based multifunctional polymer capsules

169 arises from spontaneous rearrangement of an oxazoline precursor.

170 tarting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates.

171 C-H activation of t-Bu- and i-Pr-substituted oxazolines provided good agreement with the experimental

172 The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxida

173 kN-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline (R-5b) and NaBAr(4) (5 mol %) catalyzed the as

174 [N-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] [(R)-2] and NaBAr(4) [Ar = 3,5-C(6)H(3)(CF(3)

175 ric Negishi cross-couplings (a bidentate bis(oxazoline), rather than a tridentate pybox); in the case

176 Chiral oxazolines, readily available from the corresponding ami

177 eals that aryl stereodirecting groups at the oxazoline ring 4 position and additional substitution (g

178 d with proton transfer from the intermediate oxazoline ring formed in the phosphopeptide to the metal

179 The stereochemical configuration of the oxazoline ring is shown to be the major structural facto

180 he nitro group followed by hydrolysis of the oxazoline ring yielded an optically active gamma-lactam

181 corporating gem-disubstitution on one of the oxazoline rings were prepared from (S)-valine.

182 amide is heterocyclized to form thiazole and oxazoline rings, and the peptide is cleaved to yield the

183 se produces MBT derivatives with beta-methyl oxazoline rings.

184 ng interactions to the nitrogen atoms of the oxazoline rings.

185 ce mechanisms with doubly amphiphilic poly(2-oxazoline)s (POx), a safe and highly efficient polymer f

186 Poly(2-oxazoline)s (POxs) are a versatile class of biocompatibl

187 cturally similar amphiphiles based on poly(2-oxazoline)s and poly(2-oxazine)s with respect to their s

188 on amphiphilic triblock copolymers of poly(2-oxazoline)s with orthogonal functional groups on the sid

189 imple transformation: conversion to a chiral oxazoline, SeO2-promoted oxidative rearrangement to the

190 Zn(PO4)](+), [LZn2(PO4)], and 2,4-dimethyl-3-oxazoline showing that [LGa2(PO4)](2+) is the only compo

191 to suppress the formation of trichloromethyl oxazoline side product and enable high glycosylation yie

192 ters were determined for both thiazoline and oxazoline substrates, with k(cat) values ranging between

193 A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyze

194 Oxazolines syn-2 were transformed to C-quaternary threon

195 Two conventional methods for oxazoline synthesis were also applied to generate more t

196 Three different syntheses of the phosphine oxazoline systems 1 are presented.

197 hreonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic

198 efficiently transfer the complex-type glycan oxazoline to a GlcNAc peptide and GlcNAc-containing ribo

199 a revision of the reported structure from an oxazoline to an isoxazolidinone.

200 edefined N-glycans from corresponding glycan oxazolines to the Fc-deglycosylated intact IgGs without

201 catalyzing the oxidation of thiazolines and oxazolines to yield fully aromatic heterocycles.

202 cores were prepared from amphiphilic poly(2-oxazoline) triblock copolymers.

203 uccessfully converted into the corresponding oxazolines, under milder and less wasteful conditions th

204 first reported oligomer of [2,4']-coupled 2-oxazoline units.

205 ntly developed a method for the synthesis of oxazolines using resin capture and ring-forming release

206 es and aminoalcohols to access 2-substituted oxazolines was investigated.

207 of IgG1-Fc when an excess of oligosaccharide oxazolines was used as the donor substrates.

208 bstitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due

209 Overall, eight different phosphine oxazolines were prepared.

210 First, an array of large oligosaccharide oxazolines were synthesized and evaluated as substrates

211 acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino al

212 ions through ring-opening of 4-benzylidene-2-oxazolines with Sc(OTf)3.

213 od includes the chemical synthesis of glycan oxazolines with varied number and location of the M6P mo

214 acid-catalyzed hydrolysis of poly(2-ethyl-2-oxazoline), yielding the pure polycations.