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Synfacts 2009(3): 0287-0287  
DOI: 10.1055/s-0028-1087753
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Bismuth-Catalyzed Diastereoselective SN1-Type Reaction

Contributor(s): Mark Lautens, Jane Panteleev
P. Rubenbauer, E. Herdtweck, T. Strassner, T. Bach*
Technische Universität München, Garching and Technische Universität Dresden, Germany
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

While diastereoselective nucleophilic addition to chiral benzylic cations are known (i.e., N. N. Tsou and co-workers Org. Lett. 2008, 10, 3037), such additions to other stabilized carbocations have received less attention. The authors report the bismuth-catalyzed SN1-type reaction of chiral propargylic acetates (1), yielding products in high yield and diastereoselectivity.