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Synfacts 2008(9): 0962-0962  
DOI: 10.1055/s-2008-1078640
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Zn-Catalyzed Alkynylation of N-Sulfonyl Aldimines

Contributor(s): Mark Lautens, Valentina Aureggi
G. Blay, L. Cardona, E. Climent, J. R. Pedro*
University of València, Spain
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

The enantioselective dimethylzinc-mediated catalytic alkynylation of imines has been the subject of considerable study (C. Bolm and co-workers Chem. Eur. J. 2007, 13, 2587), and building on previous work, a new variant N-sulfonyl imines is reported. A variety of aromatic and heteroaromatic N-sulfonyl aldimines and alkynes give the corresponding products in high yields and selectivities. The N-tosyl protecting group can be easily removed to give the corresponding amines without loss of optical purities.