Asymmetric 1,4‐conjugation addition of diethylzinc to cyclic enones catalyzed by a self‐assembled copper complex |
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Authors: | Shaohua Gou Zhongbin Ye Zhiyu Huang |
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Institution: | 1. School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500, People's Republic of China;2. State Key Lab of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu 610500, People's Republic of China |
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Abstract: | A new self‐assembled catalyst system based on copper complex was developed for the 1,4‐conjugation addition of diethyl zinc to cyclic enones. The self‐assembled catalyst was readily prepared from (R)‐1,1′]binaphthalenyl‐2,2′‐diamine (1a), (L )‐tryptophan (3f) and copper(I) chloride (CuCl). Several enones were found to be suitable substrates in the presence of the self‐assembled copper catalyst 10 mol% (R)‐1a, 10 mol% (L )‐3f and 10 mol% CuCl] under optimized conditions. The desired products were afforded with high isolated yields (up to 98%) and moderate to good enantioselectivities (up to 80% ee) in mild conditions (at 0 °C). Copyright © 2009 John Wiley & Sons, Ltd. |
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Keywords: | addition reaction conjugation copper enones zinc |
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