Participation of an organosulfur functionality in asymmetric Pauson-Khand reactions using (S)-methionine-derived amides as enantiocontrollable substrates

被引：21

作者：

Hiroi, K ^{[1
]}

Watanabe, T ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Dept Synthet Organ Chem, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)00521-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric Pauson-Khand reaction was successfully accomplished using chiral phenylpropiolic carboxamides derived from (S)-methionine. Participation of the organosulfur functionality with cobalt catalysts in the asymmetric Pauson-Khand reaction is clearly demonstrated, giving the corresponding Pauson-Khand reaction products with extremely high diastereoselectivity in comparison to other substrates without similar sulfenyl groups. The absolute configuration of the newly created chiral carbon centers was determined by X-ray crystallographic analysis. The mechanism for the asymmetric induction is proposed on the basis of the stereochemistry of the reactions determined by us. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3935 / 3939

页数：5

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