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Copper(I) Hydride-Catalyzed Asymmetric Hydrosilylation of Heteroaromatic Ketones

Bruce H. Lipshutz*, Asher Lower and Kevin Noson

*Department of Chemistry and Biochemistry, University of California - Santa Barbara, Santa Barbara, California 93106, Email: lipshutzchem.ucsb.edu

B. H. Lipshutz, A. Lower, K. Noson, Org. Lett., 2002, 4, 4045-4048.

DOI: 10.1021/ol026755n (free Supporting Information)


Abstract

A complex of CuH and Takasago's nonracemic ligand, DTBM-SEGPHOS, is an especially reactive reagent for the asymmetric hydrosilylation of heteroaromatic ketones under very mild conditions. PMHS serves as an inexpensive source of hydride for the in situ generation of CuH.

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Tweaking Copper Hydride (CuH) for Synthetic Gain. A Practical, One-Pot Conversion of Dialkyl Ketones to Reduced Trialkylsilyl Ether Derivatives

B. H. Lipshutz, C. C. Caires, P. Kuipers, W. Chrisman, Org. Lett., 2003, 5, 3085-3088.

Nonracemic Diarylmethanols From CuH-Catalyzed Hydrosilylation of Diaryl Ketones

C.-T. Lee, B. H. Lipshutz, Org. Lett., 2008, 10, 4187-4190.


Key Words

Hydrosilylation, PMHS, CuH, Reduction


ID: J54-Y2002-350