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Copper Hydride-Catalyzed Tandem 1,4-Reduction/Alkylation Reactions

✍ Scribed by Bruce H. Lipshutz; Will Chrisman; Kevin Noson; Patrick Papa; Joseph A. Sclafani; Randall W. Vivian; John M. Keith

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
293 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐExposure of an enone to a catalytic quantity of [CuH(PPh 3 )] 6 in the presence of one of several silyl hydrides (PhMe 2 SiH, PMHS, HMe 2 SiOSiMe 2 H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a Lewis acid at low temperatures in the presence of an aldehyde, or with ¯uoride ion together with an activated halide, affords good yields of the product of 3-component coupling (3-CC) in a single reaction ¯ask.

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