ANTI-MICHAEL ADDITION OF CYANOCUPRATE TBUCU(CN)LI TO ACCEPTOR-SUBSTITUTED ENYNES

Authors
GEROLD A KRAUSE N
Citation
A. Gerold et N. Krause, ANTI-MICHAEL ADDITION OF CYANOCUPRATE TBUCU(CN)LI TO ACCEPTOR-SUBSTITUTED ENYNES, Chemische Berichte, 127(8), 1994, pp. 1547-1549
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Chemische Berichte → ACNP
ISSN journal
00092940
Volume
127
Issue
8
Year of publication
1994
Pages
1547 - 1549
Database
ISI
SICI code
0009-2940(1994)127:8<1547:AAOCTT>2.0.ZU;2-Z
Abstract
Acceptor-substituted enynes 1 react with lithium tert-butylcyanocuprat e [tBuCu(CN)Li] in THF to afford anti-Michael adducts 3. The formation of the isomeric side products 4 can be suppressed by regioselective p rotonation of the organometallic intermediates with ethanol at -80-deg rees-C. Evidence for radical intermediates or electron-transfer steps in these reactions could not be obtained.