Synfacts 2006(3): 0259-0259  
DOI: 10.1055/s-2006-932009
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Zn-Catalyzed Asymmetric Alkynylation of Unsaturated Aldehydes

Contributor(s): Paul Knochel, Andrei Gavryushin
B. M. Trost*, A. H. Weiss, A. J. von Wangelin
Stanford University, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Enantiopure propargylic alcohols are important intermediates in asymmetric synthesis, and efficient, especially catalytic, methods for their synthesis are highly valuable. Among the most straightforward routes is a catalytic addition of alkynes to aldehydes. However, its scope is not sufficiently broad so far. In this method, a wide range of alkynes and aldehydes can be used, including α,β-enals, which are usually poor substrates for such reactions. The catalyst applied is easily available and in most cases excellent enantioselectivities can be achieved.