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Molecules 2013, 18(12), 15422-15433; doi:10.3390/molecules181215422
Article

Highly Enantioselective Addition of Phenylethynylzinc to Aldehydes Catalyzed by Chiral Cyclopropane-Based Amino Alcohols

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1,* , 1,*  and 1
1 Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, China 2 Yanlin Agriculture Bureau, 20 Huadu Avenue, Yanlin 461200, Henan, China
* Authors to whom correspondence should be addressed.
Received: 18 November 2013 / Revised: 28 November 2013 / Accepted: 29 November 2013 / Published: 11 December 2013
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Abstract

The enantioselective addition of phenylethynylzinc to aldehydes catalyzed by a series of cyclopropane-based amino alcohol ligands 7 was investigated. The reactions afforded chiral propargylic alcohols in high yields (up to 96%) and with excellent enantioselectivities (up to 98% ee) under mild conditions. Furthermore, studies on the structural relationship show that the matching of the chiral center configuration is crucial to obtain the high enantioselectivity.
Keywords: alkynylation; aldehydes; cyclopropane-based; amino alcohols; asymmetric catalysis alkynylation; aldehydes; cyclopropane-based; amino alcohols; asymmetric catalysis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zheng, B.; Li, Z.; Liu, F.; Wu, Y.; Shen, J.; Bian, Q.; Hou, S.; Wang, M. Highly Enantioselective Addition of Phenylethynylzinc to Aldehydes Catalyzed by Chiral Cyclopropane-Based Amino Alcohols. Molecules 2013, 18, 15422-15433.

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