Chemodivergence in enantioselective desymmetrization of diazabicycles: Ring-opening versus reductive arylation

被引：99

作者：

Menard, Frederic ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 11期

关键词：

asymmetric catalysis; C-H activation; desymmetrization; rhodium; ring-opening reactions;

D O I：

10.1002/anie.200704708

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Divergent bicycle paths: A chemodivergent desymmetrization occurs after an initial enantioselective carbometalation step. The reaction brings a solution to the challenging problem of the enantioselective ring-opening of diazabicyclo-[2.2.1]heptanes to obtain arylated cyclopentenamines (see scheme, right). An alternative reaction pathway was discovered in which C-H insertion/1,4-metal migration occurs to give reductive arylation products (left). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2085 / 2088

页数：4

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