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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

1
, 2
, 1
, 1
, 1
, 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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