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

Exposure of an enone to a catalytic quantity of [CuH(PPh 3)] 6 in the presence of one of several silyl hydrides (PhMe 2SiH, PMHS, HMe 2SiOSiMe 2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 18; pp. 2779 - 2788
Main Authors Lipshutz, Bruce H., Chrisman, Will, Noson, Kevin, Papa, Patrick, Sclafani, Joseph A., Vivian, Randall W., Keith, John M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.04.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
conjugate reduction
copper hydride
Physical Sciences
Science & Technology
silyl hydrides
silyl hydrides
copper hydride
conjugate reduction
KETONES
NICKEL
CHEMOSELECTIVE HYDROGENATION
ALDOL REACTION
<(PH3P)CUH>6
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
ALPHA
ALDEHYDES
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Summary:Exposure of an enone to a catalytic quantity of [CuH(PPh 3)] 6 in the presence of one of several silyl hydrides (PhMe 2SiH, PMHS, HMe 2SiOSiMe 2H) 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 fluoride ion together with an activated halide, affords good yields of the product of 3-component coupling (3-CC) in a single reaction flask.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00132-0