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
收藏
页码：7013 / 7017
页数：5
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