Stereoselective hydrogenation of α-sulfinyl radical generated from alkyl radical addition to α-(1-hydroxyethyl)vinyl sulfoxide

被引：19

作者：

Mase, N ^{[1
]}

Wake, S ^{[1
]}

Watanabe, Y ^{[1
]}

Toru, T ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(98)01118-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (2S,S-S)-alpha-(1-hydroxyethyl)vinyl sulfoxide with alkyl radicals and tributyltin hydride gave the addilion-hydrogenation products with high diastereoselectivity, whereas (2R,S-S)-alpha-(-1-hydroxyethyl)vinyl sulfoxide gave no products under similar conditions. An important role of intramolecular hydrogen bonding for the diastereoselectivity as well as the reactivity toward alkyl radicals is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5553 / 5556

页数：4

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