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Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS-Ligated CuH

Bruce H. Lipshutz,* Jeff M. Servesko, Tue B. Petersen, Patrick P. Papa and Andrew A. Lover

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, Email:

B. H. Lipshutz, J. M. Servesko, T. B. Petersen, P. P. Papa, A. A. Lover, Org. Lett., 2004, 6, 1273-1275.

DOI: 10.1021/ol04000185


Catalytic amounts of copper hydride ligated by a nonracemic SEGPHOS ligand leads in situ to an extremely reactive species capable of effecting asymmetric hydrosilylations of conjugated cyclic enones with very high enantioselectivity.

see article for more examples

Asymmetric 1,4-Hydrosilylations of α,β-Unsaturated Esters

B. H. Lipshutz, J. M. Servesko, B. R. Taft, J. Am. Chem. Soc., 2004, 126, 8352-8353.

Key Words

1,4-Reduction, Enones, PMHS, CuH

ID: J54-Y2004-340