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CuH-Catalyzed Asymmetric Conjugate Reductions of Acyclic Enones


  • We thank the NSF for financial support (CHE 0213522), and in particular Jeff Zira (UCSB) for outstanding technical assistance. We are indebted to many colleagues who generously supplied us with the ligands used in this study (Solvias “kit”: Drs. H.-U. Blaser and M. Thommen, Solvias; BIPHEP: Drs. R. Schmid and M. Scalone, Roche; SEGPHOS: Dr. T. Saito and H. Shimizu, Takasago; BoPhoz: Dr. N. Boaz, Eastman; Phanephos: Dr. P. J. Pye, Merck; BITIANP: Prof. F. Sannicolo, University of Milan; TaniaPhos: Prof. P. Knochel, Ludwig-Maximilian University, Munich).


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A powerful new reaction has been developed for the asymmetric 1,4-reduction of prochiral enones (see scheme). The key ingredients in this exceedingly mild and straightforward procedure are catalytic quantities of CuH, a readily available nonracemic phosphane ligand such as that shown, and inexpensive polymethylhydrosiloxane (PMHS) as the stoichiometric source of hydride.