A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramlecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids

被引：80

作者：

Azuma, Takumi ^{[1
]}

Murata, Akihiro ^{[1
]}

Kobayashi, Yusuke ^{[1
]}

Inokuma, Tsubasa ^{[1
,2
,3
]}

Takemoto, Yoshiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Univ Tokushima, Inst Hlth Biosci, Tokushima 7708505, Japan

[3] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 16期

关键词：

ENANTIOSELECTIVE FORMAL HYDRATION; AMIDE BOND FORMATION; 3,4,5-TRIFLUOROBENZENEBORONIC ACID; CONJUGATE ADDITION; MILD; CYCLOADDITIONS; CONDENSATION; CONVENIENT; ROUTE;

D O I：

10.1021/ol501954r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of alpha,beta-unsaturated carboxylic acids. The combination of an arylboronic add with a chiral aminothiourea allowed for these reactions to proceed successfully in an enantioselective manner to afford the desired heterocycles in high yields and ee's (up to 96% ee). The overall utility of this dual catalytic system was demonstrated by a one-pot enantioselective synthesis of (+)-erythrococcamide B, which proceeded via sequential Michael and amidation reactions.

引用

页码：4256 / 4259

页数：4

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