Copper hydride-catalyzed tandem 1,4-reduction/alkylation reactions

Authors
Lipshutz, BH Chrisman, W Noson, K Papa, P Sclafani, JA Vivian, RW Keith, JM
Citation
Bh. Lipshutz et al., Copper hydride-catalyzed tandem 1,4-reduction/alkylation reactions, TETRAHEDRON, 56(18), 2000, pp. 2779-2788
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
18
Year of publication
2000
Pages
2779 - 2788
Database
ISI
SICI code
0040-4020(20000428)56:18<2779:CHT1R>2.0.ZU;2-4
Abstract
Exposure of an enone to a catalytic quantity of [CuH(PPh3)](6) in the prese nce of one of several silyl hydrides (PhMe2SiH, PMHS, HMe2SiOSiMe2H) leads to conjugate reduction with concomitant formation of the corresponding sily l enol ether. Without isolation, treatment of these intermediates with a Le wis acid at low temperatures in the presence of an aldehyde, or with fluori de ion together with an activated halide, affords good yields of the produc t of 3-component coupling (3-CC) in a single reaction flask. (C) 2000 Elsev ier Science Ltd. All rights reserved.