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Highly Enantio- and Diastereoselective Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Allyl Ketones
Journal article   Peer reviewed

Highly Enantio- and Diastereoselective Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Allyl Ketones

Guanghu Tong, Bo Zhu, Richmond Lee, Wenguo Yang, Davin Tan, Caiyun Yang, Zhiqiang Han, Lin Yan, Kuo-Wei Huang and Zhiyong Jiang
Journal of organic chemistry, Vol.78(10), pp.5067-5072
17/05/2013
PMID: 23594149

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The alpha-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.

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