ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS THROUGH ALPHA-IODINATION OF CHIRAL UNSATURATED CARBOXAMIDES AND STEREOSELECTIVE IODOLACTONIZATION

被引：33

作者：

KITAGAWA, O ^{[1
]}

HANANO, T ^{[1
]}

KIKUCHI, N ^{[1
]}

TAGUCHI, T ^{[1
]}

机构：

[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 13期

关键词：

ASYMMETRIC IODINATION; CHIRAL PYRROLIDINE; IODOLACTONIZATION; ALPHA-AMINO ACID;

D O I：

10.1016/S0040-4039(00)60372-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the alpha-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

引用

页码：2165 / 2168

页数：4

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