ライフサイエンスコーパス: allylic alcohol

1 ed Ti-alkyne complex and a pyrone-containing allylic alcohol.

2 lenoxide to effect a 1,3-transposition of an allylic alcohol.

3 in exclusive formation of a single tricyclic allylic alcohol.

4 ighly enantioselective dihydroxylation of an allylic alcohol.

5 ows the direct coupling of readily available allylic alcohols.

6 hesis of (Z)-alpha,alpha,beta-trisubstituted allylic alcohols.

7 ehydes to produce racemic (Z)-trisubstituted allylic alcohols.

8 l Ru catalysts and enantiomerically enriched allylic alcohols.

9 tive allylation of hypophosphorous acid with allylic alcohols.

10 and other nucleophiles delivered (2Z)-2-iodo allylic alcohols.

11 nriched chiral allylic amines from prochiral allylic alcohols.

12 ved from (-)-MIB generates (Z)-disubstituted allylic alcohols.

13 ntioselectivities to generate trisubstituted allylic alcohols.

14 nylzinc reagents to aldehydes to give chiral allylic alcohols.

15 nylzinc reagents to aldehydes to give chiral allylic alcohols.

16 c methyl groups were monooxygenated to yield allylic alcohols.

17 on of variously substituted allenamides with allylic alcohols.

18 ma-disubstituted or beta,gamma-disubstituted allylic alcohols.

19 itrosobenzene to furnish nonracemic tertiary allylic alcohols.

20 -metathesis of alkyl acrylates and 2 degrees allylic alcohols.

21 electrophilic traps in the transposition of allylic alcohols.

22 rmolecular Heck-Matsuda arylation of acyclic allylic alcohols.

23 for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.

24 on of quaternary stereocenters directly from allylic alcohols.

25 The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14.

26 as not affected by Ph(3)PCl(2) conversion of allylic alcohols 13-16 into corresponding chlorides 17-2

27 tion of the enantioenriched ketone 8 to form allylic alcohol 14 was achieved by a Stille palladium-ca

28 have been completed, starting from the known allylic alcohol (+)-14, which can be prepared in large q

29 -nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a-c, aliphatic alcohols 1d-l, and benz

30 ndrost-15-en-17-one 3, via the corresponding allylic alcohol 2.

31 ylic and aliphatic alcohols 1a-1l to furnish allylic alcohols 2a-2l, constituting a direct C-H vinyla

32 couple efficiently to aldehyde 4b to provide allylic alcohols 2m-2o as single regioisomers.

33 bstrate afforded, in addition to the acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (

34 of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably p

35 beta-elimination of acetate from resin-bound allylic alcohol 3, underwent regioselective 1,3-dipolar

36 tive oxidation of 2-methyl-2-butene into the allylic alcohol, 3-methyl-2-buten-1-ol, at 90% selectivi

37 tions of alkyne 9 and aldehyde 10, affording allylic alcohols 42 or 11-epi-42 in a 3:1 ratio (or 1:3

38 of 15-acetates of the pure diastereoisomeric allylic alcohols 4a and 4b with PBr(3) occurred with sig

39 ate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the

40 e hydroxyl-directed epoxidation of tricyclic allylic alcohol 57 followed by regioselective reductive

41 ved by differential elaboration of tricyclic allylic alcohol 57.

42 desilylation with allylic transposition, the allylic alcohol 6g via protodesilylation with allylic tr

43 ogue 6, and the subsequent conversion of the allylic alcohol 7 to the chloride 8 via Ph(3)PCl(2) foll

44 elective Sharpless asymmetric epoxidation of allylic alcohol 81 (98% yield); intramolecular acetylide

45 nt intramolecular coupling to deliver cyclic allylic alcohol 8a.

46 nyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fai

47 It begins with a coupling reaction involving allylic alcohol, aldehyde, and LiHMDS to produce stereod

48 t contain a carboxylic acid, an aldehyde, an allylic alcohol, an aryl olefin, an alpha substituent, o

49 ative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in

50 Specifically, CM of allylic alcohol and enone components provides gamma-hydr

51 atalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a sing

52 -catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed.

53 irect metal-catalyzed [1,3]-transposition of allylic alcohols and allylic silyl ethers is a synthetic

54 The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented

55 s to deliver a range of synthetically useful allylic alcohols and amines in high enantiopurity.

56 anes, or ureas (derived from isocyanates and allylic alcohols and amines) as substrates.

57 alculations on the acidities of a variety of allylic alcohols and carboxylic acids support the specia

58 formation of Ru(IV) allyl intermediates from allylic alcohols and chain growth by selective nucleophi

59 hothiolate complex and afford trisubstituted allylic alcohols and ethers in up to 81% yield and >98%

60 y promoted allylic substitution reactions of allylic alcohols and ethers with diethylphosphorothioic

61 gy relies on direct use of branched, racemic allylic alcohols and furnishes a diverse and unique set

62 e also described leading to the synthesis of allylic alcohols and gamma-lactones.

63 he direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates p

64 loped regioselective [1,3]-transpositions of allylic alcohols and silyl ethers and their applications

65 zed cross-coupling between branched, racemic allylic alcohols and simple olefins is described.

66 A broad scope of phenols, various allylic alcohols, and an alkyl hydroperoxide are viable

67 The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective ald

68 yrenes, secondary allylic alcohols, tertiary allylic alcohols, and olefins with alpha-quaternary cent

69 ve transformations with an alpha-substituted allylic alcohol are shown to afford congested Z alkenes

70 Aryl allylic alcohols are converted to halogenated unsaturate

71 substrates are employed, (Z)-trisubstituted allylic alcohols are isolated with high dr (>20:1 in man

72 of thiophiles, the sulfenate is trapped, and allylic alcohols are obtained under mild conditions.

73 hen HFIP is employed as solvent and aromatic allylic alcohols are the substrates.

74 The resulting allylic alcohols are then transformed into the correspon

75 (Z)-trisubstituted allylic alcohols are widespread structural motifs in nat

76 Stille cross-coupling leads to a nonracemic allylic alcohol as a prerequisite for the introduction o

77 erived from Katsuki-Sharpless epoxidation of allylic alcohols as initiating groups for cationic cycli

78 -propanol (HFIP), polyene cyclizations using allylic alcohols as initiators gave the desired cyclized

79 asymmetric cyclopropanation of (E)- and (Z)-allylic alcohols as the key step.

80 lization, owing to the utility of enones and allylic alcohols as versatile intermediates, and their p

81 regio- and stereoselective transposition of allylic alcohols based on rhenium catalysis has been dev

82 Thus, enantioenriched tertiary allylic alcohols bearing a variety of functional groups

83 Allylic alcohols bearing a Z-iodoalkenyl tether can be s

84 even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group availabl

85 e involves a desilylation of a TBS-protected allylic alcohol, borylation, and addition of an allyl gr

86 d which was readily converted to the derived allylic alcohol by oxidative workup.

87 Asymmetric V-catalyzed epoxidation of allylic alcohols can be carried out in water with chiral

88 thyl and alpha-cyclohexyl (Z)-trisubstituted allylic alcohols can now be synthesized with excellent l

89 ion of readily available starting materials (allylic alcohols, chlorophosphites, and organic azides),

90 utyl hydroperoxide and tin(IV) chloride upon allylic alcohols containing a lactam ring leads mainly t

91 terminal alkynes and allyl vinyl ethers into allylic alcohols containing up to three contiguous asymm

92 s were found in which secondary and tertiary allylic alcohols could be formed with high levels of ena

93 1,2-disubstituted alkenes, including simple allylic alcohols, deliver syn-dichlorides with exquisite

94 reducing reagent gave a very functionalized allylic alcohol derivative in 86% yield.

95 hydes and allenes, providing silyl-protected allylic alcohol derivatives possessing a terminal methyl

96 Using this method, a number of allylic alcohol derivatives were efficiently obtained wi

97 ium-catalyzed allylic alkylation of tertiary allylic alcohol derivatives with a cyanohydrin pronucleo

98 ing groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents.

99 The development of an enantioselective allylic alcohol dichlorination catalyzed by dimeric cinc

100 antioselective bromochlorination reaction of allylic alcohols, employing readily available halogen so

101 r delta-chiral amines from readily available allylic alcohols, esters and ethers using a reductive re

102 free preparation of carbon-carbon bonds from allylic alcohols/ethers and Grignard reagents is describ

103 This included the coupling of allylic alcohols for the first time in a Pd-catalyzed co

104 oss-coupling reactions of acyclic and cyclic allylic alcohols for the stereoselective introduction of

105 For instance, (E)- and (Z)-allylic alcohols furnish the corresponding aldehydes wit

106 g-chain fatty acid alkene that also bears an allylic alcohol group.

107 Although [1,3]-transposition of allylic alcohols has been known since the late 1960s, th

108 a(3)-allyl)palladium complexes directly from allylic alcohols has been studied.

109 eOSiPh(3), 1) catalyzed 1,3-isomerization of allylic alcohols has been thoroughly explored.

110 ective coupling reactions between imines and allylic alcohols have been developed.

111 strate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylami

112 selective synthetic methods: (1) Ti-mediated allylic alcohol-imine reductive cross-coupling and (2) i

113 ent the first application of a TBS-protected allylic alcohol in a palladium-catalyzed borylation/ally

114 e direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (H

115 orkup allows isolation of B(pin)-substituted allylic alcohols in 70-95% yield.

116 reactions to provide densely functionalized allylic alcohols in good to excellent yields.

117 e a range of optically active functionalized allylic alcohols in good yields and high ee's.

118 Direct activation of allylic alcohols in the presence of transition metal cat

119 ne 2 gives primarily cyclopentanone and some allylic alcohol, in similar amounts as the known cyclohe

120 sformations that directly generate acyclic Z allylic alcohols, including products that contain a hind

121 Conversion of the product allylic alcohol into the allylic phosphate affords excel

122 (eta(2)-Allylic alcohol)iridium(I) and (eta(3)-allyl)iridium(III

123 The starting allylic alcohol is converted to its trichloroacetimidate

124 This allylic alcohol is then utilized in a Claisen rearrangem

125 ic enantioselective dichlorination of simple allylic alcohols is described.

126 mino aldehydes from allylic amines or linear allylic alcohols is described.

127 Under these conditions, deoxyfluorination of allylic alcohols is effected with high chemoselectivity

128 aration of enantioenriched (Z)-disubstituted allylic alcohols is introduced.

129 ective Ir-catalyzed isomerization of primary allylic alcohols is reported.

130 stereochemical information contained in the allylic alcohols is transferred to the ketone products.

131 oprene to 1-nonanol, 65% isolated yield) and allylic alcohols (isoprene to geraniol, 75% isolated yie

132 Not unexpectedly, applying the method to allylic alcohols leads to fragmentation rather than a di

133 was also achieved by utilizing the unreacted allylic alcohol obtained during the Sharpless kinetic re

134 These reactions provide either allylic alcohol or homoallylic alcohol derivatives selec

135 lylboronate can be oxidized to stereodefined allylic alcohols or can be used in stereoselective carbo

136 kylation products derived from 2-substituted allylic alcohols or their corresponding iodides can then

137 with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonra

138 basis for the increased facility with which allylic alcohols participate in olefin metathesis proces

139 A range of allylic alcohols participates in the diastereoselective

140 ar to that obtained from 3, yields primarily allylic alcohol rather than ketone; neither ring size no

141 The B(pin)-substituted allylic alcohols react with NBS to afford (E)-alpha,beta

142 s enable the synthesis of either (Z)- or (E)-allylic alcohols regarding the order of introducing coup

143 By this system the formation of the allylic alcohol side product and the racemization of the

144 3]-rearrangements, the stereochemistry in an allylic alcohol starting material is transferred with fi

145 of the products is a complex function of the allylic alcohol structure and is consistent with a mecha

146 The effects of allylic alcohol structure, type of vinylating agent, and

147 rearrangement was observed with a secondary allylic alcohol substrate.

148 for a wide variety of secondary and tertiary allylic alcohol substrates bearing aryl, alkyl, and cyan

149 The racemic allylic alcohol substrates can be converted to the enant

150 al beta-alkynyl carbonyl compounds employing allylic alcohol substrates in contrast to more tradition

151 reodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.

152 e enzymes catalyze the oxidation of aromatic allylic alcohols, such as coumaryl, sinapyl, and conifer

153 his is a reliable and predictable method for allylic alcohol synthesis.

154 tuted and functionalized styrenes, secondary allylic alcohols, tertiary allylic alcohols, and olefins

155 d catalytic vinylation of aldehydes leads to allylic alcohols that are then transformed to the allyli

156 noallylation step of amines with substituted allylic alcohols that proceeds to yield the monoallylate

157 ized by anti-dichlorination of the precursor allylic alcohols; their stereochemistry was elucidated b

158 ld be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetri

159 nce of CuCN, and conversion of the resultant allylic alcohol to the acetate affords good syn:anti pro

160 nslate the stereochemical information of the allylic alcohol to the homoallylic amine or to control d

161 stereoselective method for the conversion of allylic alcohols to (Z)-trisubstituted alkenes is presen

162 enantioselective isomerization of secondary allylic alcohols to access ketones with a alpha-tertiary

163 nted that catalytically oxidize benzylic and allylic alcohols to aldehydes with O2 under mild conditi

164 ve catalyst for asymmetric isomerizations of allylic alcohols to aldehydes, furnishing improved yield

165 ion between beta-iodoenamide derivatives and allylic alcohols to generate beta-allyloxyenamide deriva

166 A ferrocenium boronic acid salt activates allylic alcohols to generate transient carbocations that

167 olecular coupling of oxygen nucleophiles and allylic alcohols to give beta-aryloxycarbonyl compounds

168 lly challenging substrate class of protected allylic alcohols to the corresponding acyloin products.

169 e carboxylic acid and the sensitivity of the allylic alcohol toward elimination.

170 L/D280K) that converts stearoyl-ACP into the allylic alcohol trans-isomer (E)-10-18:1-9-OH via a cis

171 idge as well as a challenging late-stage 1,3-allylic alcohol transposition.

172 An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer condi

173 Allylic alcohols undergo transposition reactions in the

174 was used to provide the C(2)(-)C(3)(-)C(12) allylic alcohol unit characteristic of the lycorine alka

175 The synthesis of beta-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction

176 al phosphoric acid catalyzed fluorination of allylic alcohols using aryl boronic acids as transient d

177 technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated cat

178 ctive arylative semipinacol rearrangement of allylic alcohols using diaryliodonium salts is reported.

179 the Simmons-Smith fluorocyclopropanation of allylic alcohols using difluoroiodomethane and ethylzinc

180 eadily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to

181 Directed reduction of the chiral allylic alcohols using Red-Al gives exclusively the 1,2-

182 hed products furnishes secondary or tertiary allylic alcohols, valuable small molecules that cannot b

183 hyl-2-butene oxide affords the corresponding allylic alcohol via a monosolvated monomer in THF and a

184 ralins from readily available alkyne-derived allylic alcohols via consecutive multibond-forming tande

185 selective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been

186 ydes can be obtained directly from protected allylic alcohols via palladium-catalyzed autotandem reac

187 dium-mediated deoxygenation of the resulting allylic alcohol was followed by adjustment of protecting

188 productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate mo

189 thesis of allylic silanes and boronates from allylic alcohols was investigated.

190 By using this aqueous protocol, a range of allylic alcohols were epoxidized with up to 94% ee.

191 In this fashion, (Z)-disubstituted allylic alcohols were obtained with up to 98% ee.

192 It was found that the resulting allylic alcohols were racemic, most likely due to a rapi

193 The obtained allylic alcohols were transformed into conjugated alkeny

194 e from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isome

195 cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that

196 Cross-coupling of an allylic alcohol with a vinylsilane or styrene derivative

197 -disubstituted furan directly; (ii) CM of an allylic alcohol with an enone to provide an isolated gam

198 ion of dieneoxide ester (E)-7 to the 1 alpha-allylic alcohol with an exocyclic double bond (E)-8.

199 are generated from the reaction of a second allylic alcohol with high selectivity in moderate to goo

200 metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (g

201 Arylations of enals generated allylic alcohols with 81-90% ee.

202 lection in the coupling reactions of achiral allylic alcohols with chiral imines.

203 atalyzed direct dehydrative coupling between allylic alcohols with electron-deficient amines has been

204 ct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ.

205 o catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from

206 o catalyze the formation of 15 different (E)-allylic alcohols with enantioselectivities that ranged f

207 and were found to provide the desired chiral allylic alcohols with good regioselectivity and ee in ma

208 Treatment of crude gamma,gamma-disubstituted allylic alcohols with NaOH, followed by acidification, a

209 o the reactions of the analogous carbocyclic allylic alcohols with tert-butyl hydroperoxide-VO(acac)2

210 n allylic substitutions of branched, racemic allylic alcohols with various nucleophiles.