Asymmetric Michael Addition Reaction of α-Aryl-Substituted Lactams Catalyzed by Chiral Quaternary Ammonium Salts Derived from Cinchona Alkaloids: A New Short Synthesis of (+)-Mesembrine

被引：13

作者：

Nunokawa, Shiori ^{[1
]}

Minamisawa, Masamitsu ^{[1
]}

Nakano, Keiji ^{[1
]}

Ichikawa, Yoshiyasu ^{[1
]}

Kotsuki, Hiyoshizo ^{[1
]}

机构：

[1] Kochi Univ, Fac Sci, Lab Nat Prod Chem, Kochi 7808520, Japan

来源：

SYNLETT | 2015年 / 26卷 / 16期

关键词：

asymmetric organocatalysis; lactams; Michael addition; cinchona alkaloids; mesembrine; ENANTIOSELECTIVE CONSTRUCTION; STEREOSELECTIVE CONSTRUCTION; ALLYLIC ALKYLATION; CARBON-CENTERS; N-HETEROCYCLES; STEREOCENTERS; CYCLIZATIONS; BEARING; KETONES;

D O I：

10.1055/s-0035-1560090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective Michael addition reaction of alpha-aryl-substituted lactams with electron-deficient olefins was efficiently catalyzed using chiral quaternary ammonium salts derived from cinchona alkaloids. This method was highly useful for the construction of an all-carbon-substituted quaternary carbon stereogenic center at the alpha-position of lactams in good to high yields and with good enantiomeric excess and could be applied to the short synthesis of (+)-mesembrine.

引用

页码：2301 / 2305

页数：5

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