Organic Chemistry Portal



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

Bruce H. Lipshutz,* Jeff M. Servesko and Benjamin R. Taft

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

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

DOI: 10.1021/ja049135l


A complex of catalytic amounts of CuH with a nonracemic JOSIPHOS or SEGPHOS ligand leads to exceedingly efficient and highly enantioselective 1,4-reductions of α,β-disubstituted enoates and lactones using PMHS as the stoichiometric reducing agent.

see article for more examples

see article for more reactions

Asymmetric CuH-Catalyzed 1,4-Reductions in Water at Room Temperature

S. Huang, K. R. Voigtritter, H. B. Unger, B. H. Lipshutz, Synlett, 2010, 2041-2044.

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

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

Key Words

1,4-Reductions, Enones, PMHS, CuH

ID: J48-Y2004-1560