Addition of Z-vinylic higher order cyanocuprates to enones followed by O-functionalization

Authors
Moraes, DN Barrientos-Astigarraga, RE Castelani, P Comasseto, JV
Citation
Dn. Moraes et al., Addition of Z-vinylic higher order cyanocuprates to enones followed by O-functionalization, TETRAHEDRON, 56(21), 2000, pp. 3327-3337
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
21
Year of publication
2000
Pages
3327 - 3337
Database
ISI
SICI code
0040-4020(20000519)56:21<3327:AOZHOC>2.0.ZU;2-D
Abstract
Transmetalation reaction between Z-vinylic tellurides and higher order cyan ocuprates generated the corresponding Z-vinylic cyanocuprates. Conjugate ad dition of these cuprates to enones followed by O-functionalization led to s ilyl enol ethers, vinyl phosphates and vinyl triflates. The vinyl triflates were transformed into highly unsaturated systems by coupling with alkynes or with Z-vinyl zinc chlorides under Pd (0) catalysis. (C) 2000 Elsevier Sc ience Ltd. All rights reserved.