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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: lipshutzchem.ucsb.edu

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


Abstract

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.

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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