Organocatalytic Asymmetric Vinylogous Aldol Reaction of Allyl Aryl Ketones to Silyl Glyoxylates

被引：34

作者：

Han, Man-Yi ^{[1
]}

Luan, Wen-Yu ^{[1
]}

Mai, Pei-Lin ^{[1
]}

Li, Pinhua ^{[1
]}

Wang, Lei ^{[1
,2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 03期

基金：

中国国家自然科学基金;

关键词：

SILICON; EFFICIENT; ACIDS; CHEMISTRY; ADDITIONS; REAGENTS; SILANES;

D O I：

10.1021/acs.joc.7b02546

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct organocatalytic asymmetric vinylogous aldol reaction of allyl aryl ketones to silyl glyoxylates has been developed through the bifunctional catalyst, giving the alpha-hydroxysilanes with excellent enantioselectivity (up to 95% ee) and in high yields (up to 96%). The success of this catalytic methodology offers an opportunity to tackle the problems in the nucleophilic addition to acylsilanes. To activate both allyl aryl ketones and acylsilanes, the utilized bifunctional catalyst was an ideal organocatalyst in this unprecedented transformation.

引用

页码：1518 / 1524

页数：7

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