Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes

被引：28
|
作者：
Panger, Jesse L. [1 ]
Denmark, Scott E. [1 ]
机构：
[1] Univ Illinois, Roger Adams Lab, 600 South Mathews Ave, Urbana, IL 61801 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 07期
基金：
美国国家卫生研究院;
关键词：
INTRAMOLECULAR SULFENOAMINATION; SULFENOFUNCTIONALIZATION; ACIDS;
D O I：
10.1021/acs.orglett.9b04347
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the catalytic, enantioselective, intramolecular 1,2-sulfenoamidation of alkenes is described. Lewis base activation of a suitable sulfur electrophile generates an enantioenriched, thiiranium ion intermediate from a beta,gamma-unsaturated sulfonyl carboxamide. This intermediate is subsequently intercepted by the sulfonamide nitrogen resulting in cyclization to form gamma-lactams. Electron-poor alkenes required the use of a new selenophosphoramidate Lewis base catalyst. Subsequent manipulations of the products harness the latent reactivity of both the amide and thioether functionality.
引用
收藏
页码：2501 / 2505
页数：5
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