Diasterodivergent synthesis of optically pure vinyl episulfides and β-hydroxy thiocyanates from a bacterial metabolite

被引：34

作者：

Bellomo, Ana ^{[1
]}

Gonzalez, David ^{[1
]}

机构：

[1] Univ Republica, Dept Quim Organ, Fac Quim, Montevideo, Uruguay

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 17期

关键词：

D O I：

10.1016/j.tetlet.2007.02.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diasterodivergent episulfides were chemoenzymatically derived from bromobenzene by sequential toluene dioxygenase dihydroxylation, followed by chemical epoxidation and thiolysis. The epoxide ring-opening by thiocyanate ion under literature conditions rendered the corresponding hydroxy thiocyanates and not the thiiranes as usually observed. Ring closing under carefully optimized conditions allowed the preparation of optically pure thiiranes that are key precursors for the preparation of thioconduritols and pseudodisaccharides. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3047 / 3051

页数：5

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