Enantioselective Horner-Wadsworth-Emmons reaction using chiral lithium 2-aminoalkoxides

被引：0

作者：

Kumamoto, T ^{[1
]}

Koga, K ^{[1
]}

机构：

[1] UNIV TOKYO, FAC PHARMACEUT SCI, BUNKYO KU, TOKYO 113, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1997年 / 45卷 / 04期

关键词：

chiral base; chiral lithium 2-aminoalkoxide; Horner-Wadsworth-Emmons reaction; enantioselective asymmetric synthesis; chiral axis;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chiral lithium 2-aminoalkoxides ((1R,2S)-4) were applied as chiral bases for the enantioselective Horner-Wadsworth-Emmons reaction between achiral phosphonates (2) and 4-tert-butylcyclohexanone (1). A chiral olefin ((R)-3b) was obtained in up to 52% enantiomeric excess (ee). It is shown that the formation of the lithium aldolate intermediate is reversible and is not responsible for the asymmetric induction.

引用

页码：753 / 755

页数：3

共 50 条

[21] Scalable Preparation of Methylated Ando-Type Horner-Wadsworth-Emmons Reagent
Bressin, Robert K.
Driscoll, Julia L.
Wang, Yanping
Koide, Kazunori
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (02) : 274 - 277
[22] Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner-Wadsworth-Emmons reaction
Iakobson, George
Beier, Petr
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1185 - 1190
[23] Development of highly stereoselective reactions utilizing heteroatoms - New approach to the stereoselective Horner-Wadsworth-Emmons reaction
Sano, S
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2000, 120 (05): : 432 - 444
[24] (E)-Selective Horner-Wadsworth-Emmons reaction of aldehydes with bis-(2,2,2-trifluoroethyl)phosphonoacetic acid
Sano, S
Takemoto, Y
Nagao, Y
ARKIVOC, 2003, : 93 - 101
[25] Preparations of Z-α,β-unsaturated amides by using Horner-Wadsworth-Emmons reagents, (diphenylphosphono)acetamides
Ando, K
SYNLETT, 2001, (08) : 1272 - 1274
[26] Efficient Synthesis of Long-wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner-Wadsworth-Emmons Reaction
Wu, Huiqiang
Wang, Xiangmin
Liu, Yang
Zhao, Yu
Wang, Xinyue
Lee, Woo Kyoung
Shim, Young Key
Yoon, Il
Xu, Xinming
Li, Jiazhu
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2020, 41 (05) : 504 - 512
[27] Solid-phase synthesis of an N-(phenylalkyl)cinnamide library via Horner-Wadsworth-Emmons reaction
Wéber, C
Bielik, A
Szendrei, GI
Keserû, GM
Greiner, I
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) : 1279 - 1281
[28] Synthesis of Vinylene-Linked Two-Dimensional Conjugated Polymers via the Horner-Wadsworth-Emmons Reaction
Pastoetter, Dominik L.
Xu, Shunqi
Borrelli, Mino
Addicoat, Matthew
Biswal, Bishnu P.
Paasch, Silvia
Dianat, Arezoo
Thomas, Heidi
Berger, Reinhard
Reineke, Sebastian
Brunner, Eike
Cuniberti, Gianaurelio
Richter, Marcus
Feng, Xinliang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (52) : 23620 - 23625
[29] Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction
Sano, S
Takehisa, T
Ogawa, S
Yokoyama, K
Nagao, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (09) : 1300 - 1302
[30] Synthesis of Allenyl Esters by Horner-Wadsworth-Emmons Reactions of Ketenes Mediated by Isopropylmagnesium Bromide
Sano, Shigeki
Matsumoto, Tomoya
Yano, Teppei
Toguchi, Munehisa
Nakao, Michiyasu
SYNLETT, 2015, 26 (15) : 2135 - 2138

← 1 2 3 4 5 →