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Synfacts 2007(8): 0849-0849  
DOI: 10.1055/s-2007-968724
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Propargylic Alcohols

Contributor(s): Mark Lautens, Frédéric Ménard
L. Lin, X. Jiang, W. Liu, L. Qiu, Z. Xu, J. Xu, A. S. C. Chan, R. Wang*
Lanzhou University and The Hong Kong Polytechnic University, P. R. of China
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

A one-pot procedure was developed to prepare enantiomerically enriched propargylic alcohols. The method used DME as additive to accelerate the in situ alkynyl-zinc formation instead of using toxic HMPA, as in previously reported methods (A. R. Rajaram, L. Pu Org. Lett. 2006, 8, 2019). The method allowed the addition of non-aromatic alkynes to a range of aldehydes. Aromatic aldehydes showed the highest enantioselec­tivity (90-94% ee), and other aldehydes showed lower results (79-85% ee).