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)

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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.

see article for more examples

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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.

Ligand-Accelerated, Copper-Catalyzed Asymmetric Hydrosilylations of Aryl Ketones

B. H. Lipshutz, K. Noson, W. Chrisman, J. Am. Chem. Soc., 2001, 123, 12917-12918. DOI: 10.1021/ja011529e

CuH in a Bottle: A Convenient Reagent for Asymmetric Hydrosilylations

B. H. Lipshutz, B. A. Frieman, Angew. Chem. Int. Ed., 2005, 44, 6345-6348. DOI: 10.1002/anie.200500800

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Key Words

Hydrosilylation, PMHS, CuH, Reduction

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ID: J54-Y2002-350