Silver(I)-catalyzed asymmetric Mukaiyama aldol reaction

被引：0

作者：

Ohkouchi, M ^{[1
]}

Yamaguchi, M ^{[1
]}

Yamagishi, T ^{[1
]}

机构：

[1] Tokyo Metropolitan Univ, Grad Sch Engn, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

来源：

ENANTIOMER | 2000年 / 5卷 / 01期

关键词：

Ag(I)-complex; Lewis acid catalyst; Mukaiyama aldol reaction;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Cationic Ag(I)-BINAP complex has been shown to be an effective catalyst for Mukaiyama aldol reaction between aldehyde and silyl enol ether derivatives. AgPF6-BINAP is very active in this reaction and can achieve high enantiomeric excess under mild conditions. Addition of a small amount of water enhanced the reactivity to suggest the contribution of enolate anion intermediate. AgOAc-BINAP, which in non-cationic species, showed an extraordinary; high activity although %ee was low.

引用

页码：71 / 81

页数：11

共 50 条

[1] SILVER(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF ISOCYANOACETATE
HAYASHI, T
UOZUMI, Y
YAMAZAKI, A
SAWAMURA, M
HAMASHIMA, H
ITO, Y
TETRAHEDRON LETTERS, 1991, 32 (24) : 2799 - 2802
[2] Study of the Lanthanide-Catalyzed, Aqueous, Asymmetric Mukaiyama Aldol Reaction
Mei, Yujiang
Averill, Derek J.
Allen, Matthew J.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13): : 5624 - 5632
[3] A catalytic asymmetric vinylogous mukaiyama aldol reaction
Heumann, Lars V.
Keck, Gary E.
ORGANIC LETTERS, 2007, 9 (21) : 4275 - 4278
[4] Mukaiyama Aldol Reaction Catalyzed by Mesoporous Aluminosilicate
Ito, Suguru
Yamaguchi, Hitoshi
Kubota, Yoshihiro
Asami, Masatoshi
CHEMISTRY LETTERS, 2009, 38 (07) : 700 - 701
[5] THE ASYMMETRIC ALDOL REACTION OF TOSYLMETHYL ISOCYANIDE AND ALDEHYDES CATALYZED BY CHIRAL SILVER(I) COMPLEXES
SAWAMURA, M
HAMASHIMA, H
ITO, Y
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24): : 5935 - 5936
[6] Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by allo-Threonine-Derived Oxazaborolidinone
Adachi, Shinya
Harada, Toshiro
ORGANIC LETTERS, 2008, 10 (21) : 4999 - 5001
[7] Asymmetric aldol polymerization: Synthesis of optically active polymers based on the asymmetric Mukaiyama aldol reaction
Komura, K
Itsuno, S
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2002, 203 (07) : 931 - 936
[8] Efficient Mukaiyama aldol reaction by silver(I) carboxylate-bis(phosphine) catalysts
Ohkouchi, M
Masui, D
Yamaguchi, M
Yamagishi, T
NIPPON KAGAKU KAISHI, 2002, (02) : 223 - 229
[9] Asymmetric Aldol Reaction Catalyzed by a Chiral Phosphine-Silver Complex
Yanagisawa, Akira
Miyake, Ryoji
Yoshida, Kazuhiro
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (20) : 4248 - 4253
[10] Oxazaborolidinone-Mediated Asymmetric Bisvinylogous Mukaiyama Aldol Reaction
Eggert, Alina
Etling, Christoph
Millbrodt, Lucas
Schulz, Goran
Kalesse, Markus
ORGANIC LETTERS, 2021, 23 (22) : 8722 - 8726

← 1 2 3 4 5 →