Asymmetric Synthesis of Ethoxydienamines in Superbasic Medium Mediated by Chiral Sulfinyl Group

被引：3

作者：

Blangetti, Marco ^{[1
]}

Croce, Gianluca ^{[2
]}

Deagostino, Annamaria ^{[1
]}

Mussano, Eleonora ^{[1
]}

Prandi, Cristina ^{[1
]}

Venturello, Paolo ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy

[2] Univ Piemonte Orientale Amedeo Avogadro, Dipartimento Sci & Tecnol Avanzate, I-15121 Alessandria, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 06期

关键词：

SULFINIMINES; SULFOXIDES;

D O I：

10.1021/jo1024943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct addition of metalated alkoxydiene 2, obtained from alpha,beta-unsaturated acetal 1 through a LIC-KOR-promoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and S N-sulfinyl imines) afforded N-sulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure beta-keto amines 7.

引用

页码：1814 / 1820

页数：7

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