Enantioselective synthesis of cyclic allylboronates by Mo-catalyzed asymmetric ring-closing metathesis (ARCM). A one-pot protocol for net catalytic enantioselective cross metathesis

被引：29

作者：

Jernelius, JA

Schrock, RR

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

[2] MIT, Dept Chem, Cambridge, MA 02138 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 34期

关键词：

allylboronates; asymmetric cross metathesis; asymmetric ring-closing metathesis;

D O I：

10.1016/j.tet.2004.06.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mo-catalyzed asymmetric ring-closing metathesis (ARCM) reactions are used to synthesize cyclic allylboronates of high optical purity (89% ee to >98% ee). A one-pot procedure involving formation of allylboronates, Mo-catalyzed ARCM and functionalization of the optically enriched cyclic allylboronates constitutes net asymmetric cross metathesis (ACM). Structural modification of ARCM products include reactions with aldehydes to afford optically enriched compounds that bear quaternary carbon centers with excellent diastereoselectivity. These studies emphasize the significance, of the availability of chiral Mo-based complex as a class of chiral metathesis catalysts that frequently complement one another in terms of reactivity and selectivity. (C) 2004 Published by Elsevier Ltd.

引用

页码：7345 / 7351

页数：7

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