Catalytic Enantioselective N-Nitroso Aldol Reaction of γ,δ-Unsaturated δ-Lactones

被引：37

作者：

Yanagisawa, Akira ^{[1
]}

Fujinami, Takeo ^{[1
]}

Oyokawa, Yu ^{[1
]}

Sugita, Takuya ^{[1
]}

Yoshida, Kazuhiro ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 10期

关键词：

ASYMMETRIC ALPHA-AMINOXYLATION; ALPHA; ALPHA-DIPHENYLPROLINOL TRIMETHYLSILYL ETHER; ACID CATALYSIS; ALDEHYDES; KETONES; 1,2-DIOLS; HYDROXY; FACILE; RICH;

D O I：

10.1021/ol300146k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric N-nitroso aldol reaction of gamma,delta-didehydro-delta-lactones with nitrosoarenes was achieved using chiral tin dibromide as the chiral precatalyst and sodium ethoxide as the base precatalyst in the presence of ethanol. Optically active alpha-hydroxyamino ketones with up to 99% ee were regioselectively obtained in moderate to high yields from various delta-aryl-substituted gamma,delta-didehydro-delta-valerolactones and o-substituted nitrosoarenes.

引用

页码：2434 / 2437

页数：4

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