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1 a key cyclopentenone harboring a spirocyclic oxazoline.
2 ollowed by a gradual transition toward the 2-oxazoline.
3 poly-2-methyl-2-oxazoline or poly-2-ethyl-2-oxazoline.
4 e to 4-(methoxycarbonyl)-5,5-disubstituted 2-oxazoline.
5 wer GB (321 kJ/mol less) than 2,4-dimethyl-3-oxazoline.
6 dative cyclization of N-alkenylamides into 2-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 cNAc-Fc homodimer) with the synthetic glycan oxazolines.
11 rther reaction with an amine base provides 2-oxazolines.
12 cooperative effects in meta-substituted aryl oxazolines.
14 tereospecifically and regiospecifically into oxazolines (+/-)-13 and (+/-)-14 and into cyclic carbama
15 ovel method for the preparation of 4-allenyl-oxazolines 2 is described via the reaction of 2-en-4-yn-
16 ycosides having a cis-1,2-fused pyranose-1,3-oxazoline-2-thione structure and bearing different subst
21 C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidativ
22 presence of SOCl(2) produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted thiaz
23 Chiral and achiral 3-methoxynaphthalen-2-yl oxazolines 4a,b failed to undergo an aromatic nucleophil
24 e2)2 (M = Ti, Zr, Hf; Ox(R) = 4,4-dimethyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-ter
25 hyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperatur
27 , the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7).
29 reaction was employed to construct a chiral oxazoline 9 (99% yield, 98% ee) that served the dual pur
30 s diacylated product undergoes a second aryl oxazoline acylation on its remaining secondary amine, al
31 tivation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic a
32 drogenations mediated by the chiral, carbene-oxazoline analogue of Crabtree's catalyst "cat" in asymm
33 ns, together with the previously constructed oxazoline analogues 5d and 6d, were subjected to biologi
36 ed by chemical synthesis of a large N-glycan oxazoline and its subsequent enzymatic ligation to GlcNA
37 olytic activity toward both the Man(9)GlcNAc oxazoline and the product as well as to its enhanced act
38 ment of an effective and practical method of oxazoline and thiazoline formation, which can facilitate
40 trans-glycosylation using well-defined sugar oxazolines and mutant forms of endo beta-N-acetylglucosa
41 ition states with t-Bu- and i-Pr-substituted oxazolines and suggested a possible explanation for the
44 f N-acylbenzotriazoles in the preparation of oxazolines and thiazolines under mild conditions and sho
45 ono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof
46 s(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily mo
47 tammetry (CV) analyses of bidentate pyridyl, oxazoline, and imidazoline nitrogen ligands, along with
48 catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline 4-carboxylate to a nitroalke
51 )(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
54 , we introduce for the first time the use of oxazoline as a more versatile motif for this transformat
55 sing allylamine, acrylic acid and 2-methyl-2-oxazoline as precursor to produce amine, carboxyl and ox
56 rected] could not take more complex N-glycan oxazoline as substrate for transglycosylation, indicatin
57 esses transglycosylation activity with sugar oxazoline as the donor substrate, but the transglycosyla
59 ted substituents on the aromatic ring and an oxazoline as the heterocyclic moiety, demonstrated in vi
60 f the chemical synthesis of defined N-glycan oxazolines as donor substrates, the expression of the Fc
61 can still catalyse synthetic processes using oxazolines as donors, but which do not hydrolyse the rea
63 able to use both bi- and triantennary glycan oxazolines as substrates for transglycosylation, in cont
67 y diastereoselective allylation, and a novel oxazoline-assisted piperidinone forming reaction to prov
68 yl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperature and below, affording five
69 nd their derivatives, including ortho ester, oxazoline, azido epoxide, as well as sulfonamide-, amide
70 ic side chains in one block, poly(2-methyl-2-oxazoline)-b-poly(2-N,N-dimethyl-1,3,5-triazine-2,4-diam
74 oromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, o
75 general class of imino ethers that includes oxazolines, benzoxazoles and benzimidates are applicable
77 r side chain in poly(2-methoxycarboxyethyl-2-oxazoline) block (PMestOx) of the PMeOx-PMestOx diblock
78 pha,omega-hydroxy-end-capped poly(2-methyl-2-oxazoline)-block-poly(dimethylsiloxane)-block-poly(2-met
81 did not recognize the complex-type N-glycan oxazoline but could efficiently use the high-mannose-typ
83 stical copolymerization of 2-oxazines with 2-oxazolines can lead to the formation of amphiphilic grad
84 etylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamid
85 stablish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantio
86 zoic acid salts of the chiral copper(II) bis(oxazoline) catalyst deliver both diastereomers of the He
87 secondary benzyl chlorides with a Ni(II)/bis(oxazoline) catalyst in the presence of Mn(0) as a stoich
88 ass directly over the immobilized copper bis(oxazoline) catalyst without detrimentally impacting the
89 ylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-couplin
92 the stereochemical outcome of the copper-bis(oxazoline)-catalyzed C-H insertion reaction between meth
93 son, a 1:1 mixture of the palladium pyridine-oxazoline complex (N-N)Pd(Me)Cl inverted question markN-
99 tituent onto the cyclopentadienyl ring of an oxazoline-conjugated ferrocene with the stereochemical s
100 simple catalytic hydrogenation at C-1 of an oxazoline constructed from the corresponding 2-aminopyra
101 , the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration
103 the outer mannose residues of the Man3GlcNAc-oxazoline core, thus allowing introduction of large olig
105 exo-Diels-Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the
106 do selectivity enhancements delivered by bis(oxazoline)-Cu(II) Lewis acid catalysts in the Diels-Alde
107 t, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst c
109 strate its applicability in the synthesis of oxazoline derivatives through a convenient two-step proc
112 We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl o
113 stereoselectivity (>99:1 dr) observed in the oxazoline-directed, Pd(II)-catalyzed sp(3) C-H bond iodi
115 lipid A region-was synthesized using an 1,3-oxazoline donor, which was followed by coupling with an
117 the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and
118 ne-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the
119 nes and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring e
122 the epoxides were converted directly to the oxazoline form of the target molecules using a Ritter re
123 results show that controlling the balance of oxazoline formation and glycosylation is key to achievin
126 no impact on the diastereoselectivity of the oxazoline formation, and chiral triazolylidenes did not
127 A powerful method for the synthesis of 2-oxazolines from silyl-protected beta-hydroxyamides is re
130 lyzed by [Cu{(S,S)-tBu-box}](SbF6)2 [box=bis(oxazoline)] generate chiral alpha-functionalized alpha-h
131 stituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcP
135 hydes, imines, and activated olefins to form oxazolines, imidazolines, and pyrrolines, respectively.
137 c hydrogenation of substituted benzenes with oxazoline imino(pyridine) (OIP) molybdenum precatalysts
138 e converted into 2-(9'-fluorenylmethyloxy)-2-oxazoline in high yield, thereby providing a new pathway
139 oxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ,
143 cient to take various modified N-glycan core oxazolines, including the bisecting sugar-containing der
147 ition, and electrocyclic ring opening of a 4-oxazoline intermediate affords the indoloquinone 31 in a
148 structural and electronic properties of the oxazoline intermediate are similar to the known chitinas
149 s double displacement mechanism involving an oxazoline intermediate distinguishes the family 18 chiti
153 d two potential hydrolysis intermediates (an oxazoline ion and an oxocarbenium ion) to a family 19 ba
154 hevamine (a family 18 chitinase) involves an oxazoline ion intermediate stabilized by the neighboring
156 Structural and electronic features of the oxazoline ion likely to be important in the design of ne
158 ral 2,2'-(2,6-pyridinediyl)bis(4-isopropyl-2-oxazoline) (iPr-Pybox) to a self-assembled Co(II)-[W(V)(
159 mistry of the stereogenic carbon next to the oxazoline is not necessarily the dominant chiral center
160 cular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is
161 led that C(4)-phenyl substitution on the bis(oxazoline) is optimal for high asymmetric induction.
162 eed upon to be caused by an intermediate 1,2-oxazoline, is often bypassed by introducing extra synthe
163 f the substituents on the aryl moiety of the oxazoline lead to a surprising modulation of reactivity.
165 ew, readily available bidentate isoquinoline-oxazoline ligand furnishes excellent ee's and good yield
167 ontrast, complex of a finely tuned phosphino-oxazoline ligand promotes unique [2+2]-cycloaddition bet
172 Here, we describe the development of a bis(oxazoline) ligand that enables the desymmetrization of m
175 opper(I) catalyst equipped with a chiral bis(oxazoline) ligand, high yields and enantioselectivities
176 tioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselect
178 dium complexes of the N-heterocyclic carbene oxazoline ligands 1 in asymmetric hydrogenations of aryl
179 e have identified 2-(2-diarylphosphinophenyl)oxazoline ligands and mild reaction conditions for effic
180 a range of novel gem-disubstituted ferrocene-oxazoline ligands and their application in both the asym
183 ear to differ from the traditional phosphine-oxazoline ligands in that the stereochemistry of the ste
184 -disubstitution of i-Pr-containing ferrocene oxazoline ligands results in increased enantioselectivit
185 design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopro
192 mmercially available or readily prepared bis(oxazoline) ligands such as (4R,5S)-Ph(2)BoxH, (4S,5R)-Ar
195 mpounds is disclosed using a chiral pyridine oxazoline-ligated palladium catalyst under mild conditio
197 , and finally obtaining poly[oligo(2-ethyl-2-oxazoline) methacrylate]s (POEOXMAs) by reversible addit
198 hieved by first synthesizing oligo(2-ethyl-2-oxazoline) methacrylates (OEOXMAs) by cationic ring-open
199 -Me(2)Box]La[N(TMS)(2)](2) (Box = 2,2'-bis(2-oxazoline)methylenyl; Ar = 4-tert-butylphenyl, 1-naphthy
201 in the stereochemistry of their butyrate or oxazoline moieties were not recognized by human T cells.
202 n the substitution pattern on the oxazole or oxazoline moieties, mono- and dioxabacteriochlorins may
204 tral chirality, (ii) imidazoline moiety over oxazoline moiety, and (iii) phosphine unit is investigat
205 ique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to
213 er both in substrate and the [Cu(R,R)-Ph-bis(oxazoline)]OTf(2) catalyst and zero order in TEMPO.
217 ly(vinylpyrrolidone)), PMOX (poly(2-methyl-2-oxazoline)), PDMA (poly(N,N-dimethyl acrylamide)), and P
219 rther neutral polymer, namely poly(2-ethyl-2-oxazoline) (PEOz) can be successfully used as a dipole l
220 indirectly attributed to interaction of the oxazoline-phenyl substituent with the palladium and with
221 r and demonstrate that the threonine-derived oxazoline plays a critical role in determining the kinet
222 imethyl-1,3,5-triazine-2,4-diamine-6-ethyl-2-oxazoline) (PMeOx-PcBOx), and demonstrate its potential
223 c poly[(2-methyl-2-oxazine)- grad-(2-butyl-2-oxazoline)] (PMeOzi- grad-PBuOx) as well as the thermore
224 poly[(2-methyl-2-oxazine)- grad-(2-propyl-2-oxazoline)] (PMeOzi- grad-PPrOx) confirmed their potenti
225 m and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter w
228 tarting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates.
230 C-H activation of t-Bu- and i-Pr-substituted oxazolines provided good agreement with the experimental
235 The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxida
236 kN-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline (R-5b) and NaBAr(4) (5 mol %) catalyzed the as
237 [N-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] [(R)-2] and NaBAr(4) [Ar = 3,5-C(6)H(3)(CF(3)
238 ric Negishi cross-couplings (a bidentate bis(oxazoline), rather than a tridentate pybox); in the case
240 nd 13 steps, respectively, and feature a key oxazoline reduction that sets the stage for piperazine c
241 eals that aryl stereodirecting groups at the oxazoline ring 4 position and additional substitution (g
242 ition of indoles in combination with unusual oxazoline ring cleavage and subsequent 1,2-alkyl shift a
243 d with proton transfer from the intermediate oxazoline ring formed in the phosphopeptide to the metal
244 The stereochemical configuration of the oxazoline ring is shown to be the major structural facto
245 he nitro group followed by hydrolysis of the oxazoline ring yielded an optically active gamma-lactam
246 lexes [(G-PHOX)CoX(2)] (G = 4-substituent on oxazoline ring) effect selective 1,2-, 1,4-, or 4,3-addi
247 Ligand modification (substitution at the oxazoline ring) significantly enhanced the reactivity, c
249 amide is heterocyclized to form thiazole and oxazoline rings, and the peptide is cleaved to yield the
252 ce mechanisms with doubly amphiphilic poly(2-oxazoline)s (POx), a safe and highly efficient polymer f
253 nd-group diversification approach for poly(2-oxazoline)s (POx), enabling quick and reliable productio
255 based on multifunctional amphiphilic poly(2-oxazoline)s and covalently cross-linked with spiropyran
256 olymerization modification of poly(2-alkyl-2-oxazoline)s and poly(2-alkyl-2-oxazine)s using Ind*Rh(II
257 cturally similar amphiphiles based on poly(2-oxazoline)s and poly(2-oxazine)s with respect to their s
259 on amphiphilic triblock copolymers of poly(2-oxazoline)s with orthogonal functional groups on the sid
260 ine the high structural modularity of poly(2-oxazoline)s with the excellent biological properties of
262 imple transformation: conversion to a chiral oxazoline, SeO2-promoted oxidative rearrangement to the
263 Zn(PO4)](+), [LZn2(PO4)], and 2,4-dimethyl-3-oxazoline showing that [LGa2(PO4)](2+) is the only compo
264 to suppress the formation of trichloromethyl oxazoline side product and enable high glycosylation yie
265 we report a palladium(II) [Pd(II)]/sulfoxide-oxazoline(SOX)/phosphoric acid-mediated C(sp(3))H/N(sp(2
266 ters were determined for both thiazoline and oxazoline substrates, with k(cat) values ranging between
267 A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyze
271 hreonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic
272 (Cy) domains generate biologically important oxazoline/thiazoline groups found in natural products, i
273 efficiently transfer the complex-type glycan oxazoline to a GlcNAc peptide and GlcNAc-containing ribo
276 edefined N-glycans from corresponding glycan oxazolines to the Fc-deglycosylated intact IgGs without
278 ent of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and
279 ectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) a
281 uccessfully converted into the corresponding oxazolines, under milder and less wasteful conditions th
282 backbone and two stereochemically identical oxazoline units, leads to the formation of four stereois
284 directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partne
285 ntly developed a method for the synthesis of oxazolines using resin capture and ring-forming release
286 n of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of
289 bstitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due
290 l trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastere
292 First, an array of large oligosaccharide oxazolines were synthesized and evaluated as substrates
293 acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino al
294 proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines followin
295 ld leverages the intermolecular formation of oxazolines with a wide functional group tolerance on bot
296 to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity.
297 amate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium-magnesium amides followed
299 od includes the chemical synthesis of glycan oxazolines with varied number and location of the M6P mo