铜催化的氧杂双环烯烃与格氏试剂的高度对映选择性开环反应

Highly enantioselective copper-catalyzed ring opening of oxabicyclic alkenes with Grignard reagents.

作者信息

Zhang Wei, Zhu Shou-Fei, Qiao Xiang-Chen, Zhou Qi-Lin

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry Nankai University, Tianjin (China).

出版信息

Chem Asian J. 2008 Dec 1;3(12):2105-11. doi: 10.1002/asia.200800159.

DOI:10.1002/asia.200800159

PMID:18823061

Abstract

A highly efficient copper-catalyzed enantioselective ring opening of oxabicylic alkenes with Grignard reagents has been developed by using chiral spiro phosphine ligands. Excellent trans selectivities, good yields, and high enantioselectivities are obtained for a broad range of Grignard reagents under mild reaction conditions. The catalyst system shows an extraordinary activity and the TON of the reaction reaches 9000.

摘要

通过使用手性螺环膦配体，开发了一种高效的铜催化的氧杂双环烯烃与格氏试剂的对映选择性开环反应。在温和的反应条件下，对于多种格氏试剂都能获得优异的反式选择性、良好的产率和高对映选择性。该催化体系表现出非凡的活性，反应的TON达到9000。