One-step highly diastereoselective synthesis of γ-aminoalkyl-substituted γ-butyrolactones by an asymmetric samarium-mediated ketyl-alkene coupling reaction

被引：21

作者：

Fukuzawa, S ^{[1
]}

Miura, M ^{[1
]}

Saitoh, T ^{[1
]}

机构：

[1] Chuo Univ, Inst Sci & Engn, Dept Appl Chem, Bunkyo Ku, Tokyo 1128551, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 05期

关键词：

D O I：

10.1021/jo020574h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.

引用

页码：2042 / 2044

页数：3

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