Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

被引：41

作者：

Arteaga, Fernando Arteaga ^{[1
]}

Liu, Zijian ^{[1
]}

Brewitz, Lennart ^{[1
]}

Chen, Jianyang ^{[1
]}

Sun, Bo ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem Bikaken, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 10期

关键词：

ALDOL REACTION; 1,4-ADDITION REACTIONS; BETA-PEPTIDES; AMIDES; ALDEHYDES; ALKYLNITRILES; ACETONITRILE; THIOAMIDES; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.6b00879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the alpha-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

引用

页码：2391 / 2394

页数：4

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