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: lipshutz
chem.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 (free Supporting Information)
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.
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
