Highly Enantioselective Ketone-Ene Reactions of Trifluoropyruvate: Significant Counterion Effect of the In(III)-PyBox Complex

被引：37

作者：

Zhao, Jun-Feng ^{[1
]}

Tjan, Teguh-Budiono W. ^{[1
]}

Tan, Boon-Hong ^{[1
]}

Loh, Teck-Peng ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 24期

关键词：

DIELS-ALDER REACTION; CHIRAL BRONSTED ACID; MUKAIYAMA ALDOL REACTION; CARBONYL-ENE; COPPER(II) COMPLEXES; LEWIS-ACIDS; ASYMMETRIC CATALYSIS; ALLYLATION; GLYOXYLATE; ALDEHYDES;

D O I：

10.1021/ol902507x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

引用

页码：5714 / 5716

页数：3

共 13 条

[11] In(III)-pybox complex catalyzed enantioselective Mukaiyama aldol reactions between polymeric or hydrated glyoxylates and enolsilanes derived from aryl ketones
Zhao, Jun-Feng
Tan, Boon-Hong
Loh, Teck-Peng
CHEMICAL SCIENCE, 2011, 2 (02) : 349 - 352
[12] Catalytic and highly enantioselective Friedel-Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex (vol 25, pg 1104, 2014)
Aikawa, Kohsuke
Asai, Yuya
Hioki, Yuta
Mikami, Koichi
TETRAHEDRON-ASYMMETRY, 2014, 25 (18-19) : 1352 - 1353
[13] Highly Enantioselective and Anti-Diastereoselective Catalytic Intermolecular Glyoxylate-Ene Reactions: Effect of the Geometrical Isomers of Alkenes
Zhang, Xiang
Wang, Min
Ding, Ran
Xu, Yun-He
Loh, Teck-Peng
ORGANIC LETTERS, 2015, 17 (11) : 2736 - 2739

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