Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

被引：39
|
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
收藏
页码：2391 / 2394
页数：4
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