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CuH-Catalyzed Enantioselective Intramolecular Reductive Aldol Reactions Generating Three New Contiguous Asymmetric Stereocenters

Bruce H. Lipshutz*, Benjamin Amorelli and John B. Unger

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, Email: lipshutzchem.ucsb.edu

B. H. Lipshutz, B. Amorelli, J. B. Unger, J. Am. Chem. Soc., 2008, 130, 14378-14379.

DOI: 10.1021/ja8045475 (free Supporting Information)


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Abstract

Treatment of β,β-disubstituted-α,β-unsaturated ketones bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to cyclic aldol products with three newly created adjacent chiral centers. Excellent diastereoselectivities and enantioselectivities are obtained for several examples studied.

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Key Words

Cyclohexanols, Copper Hydride, DEMS


ID: J48-Y2008-3160