J. Am. Chem. Soc., 129 (3), 496 -497, 2007. 10.1021/ja0679578 S0002-7863(06)07957-1
Web Release Date: December 21, 2006

Copyright © 2006 American Chemical Society

Catalytic Enantioselective Allenylation Reactions of Aldehydes with Tethered Bis(8-quinolinolato) (TBOx) Chromium Complex

Guoyao Xia and Hisashi Yamamoto*

Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637

yamamoto@uchicago.edu

Received November 12, 2006

Abstract:

The utility of the new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is further explored. Its chromium complex, TBOxCr(III)Cl, effectively catalyzes the asymmetric allenylation reactions of various aldehydes at room temperature with high yields (up to 91%) and high enantioselectivities (up to 97% ee). The scope of the present method is shown to be wide, and this method represents an efficient access to chiral -allenic alcohols.


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