Iodomethylation of chiral alpha-amino aldehydes by means of samarium/diiodomethane. Application to the synthesis of various enantiomerically pure compounds

被引：33

作者：

Concellon, JM ^{[1
]}

Bernad, PL ^{[1
]}

PerezAndres, JA ^{[1
]}

机构：

[1] UNIV OVIEDO,FAC QUIM,INST QUIM ORGANOMET,E-33071 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 25期

关键词：

D O I：

10.1021/jo970318i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral iodohydrins 2 have been obtained from alpha-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of a-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.

引用

页码：8902 / 8906

页数：5

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