Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH••••O hydrogen bonding

被引：34

作者：

Paddon-Row, Michael N. ^{[1
]}

Kwan, Laurence C. H. ^{[2
]}

Willis, Anthony C. ^{[2
]}

Sherburn, Michael S. ^{[2
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 37期

关键词：

asymmetric catalysis; density functional calculations; Lewis acids; Lewis bases; transition states;

D O I：

10.1002/anie.200802002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7013 / 7017

页数：5

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