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Synfacts 2006(11): 1140-1140  
DOI: 10.1055/s-2006-949427
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Propargyl andα-Allenyl Alcohols from Ketones

Contributor(s): Mark Lautens, Frédéric Ménard
E. Hernandez, C. H. Burgos, E. Alicea, J. A. Soderquist*
University of Puerto Rico, Rio Piedras, Puerto Rico
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

The recent development in the preparation of isomerically pure allenyl and propargyl boranes has provided an opportunity to use the chiral borabicyclodecanes 1 and 4 for asymmetric ketone alkylation. Although the propargyl­ation with 4 shows better selectivity in many cases, the allenylation with 1 showed useful levels of selectivity, even when there is only minimal difference in the steric environments of RL vs RS (e.g., Me vs Et).