Palladium catalyzed enantioselective rearrangement of allylic imidates to allylic amides

被引：93

作者：

Hollis, TK ^{[1
]}

Overman, LE ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1999年 / 576卷 / 1-2期

关键词：

allylic amine; allylic imidate; catalysis; enantioenriched; enantioselective; palladium; 3,3]-sigmatropic rearrangement;

D O I：

10.1016/S0022-328X(98)01065-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Recent progress in developing asymmetric Pd(II) catalysts for the [3,3]-sigmatropic rearrangement of allylic imidates to form enantioenriched allylic amides is reviewed. The best catalysts developed to date generate allylic amides in > 90% enantiomeric excess (ee) from some allylic imidate substrates. The most recent catalysts developed in our laboratories are based on cyclopalladated ferrocenes having elements of planar chirality. A mechanistic proposal that enantioselection in Pd(II)-catalyzed allylic imidate rearrangements might derive from axial approach of the alkene to the chiral Pd(II) catalyst has guided our design of improved ligands. (C) 1998 Elsevier Science S.A. All rights reserved.

引用

页码：290 / 299

页数：10

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