Stereoselective desymmetrisation of prochiral alpha, alpha-dicyanoalkenes via domino Michael-Michael addition reactions

作者:Kang Tai Ran; Xie Jian Wu; Du Wei; Fenga Xin; Chen Ying Chun*
来源:Organic and Biomolecular Chemistry, 2008, 6(15): 2673-2675.
DOI:10.1039/b809308c

摘要

The desymmetrisation of prochiral alpha, alpha-dicyanoalkenes via tandem Michael-Michael addition reactions with alpha, beta-unsaturated ketones catalysed by 9-amino-9-deoxyepicinchona alkaloids was investigated, from which bicyclic products bearing four stereogenic centers were afforded in a single operation with high stereoselectivities (> 99% de, up to > 99.5% ee).