(CYANOMETHYLENE)PHOSPHORANES AS NOVEL CARBONYL 1,1-DIPOLE SYNTHONS - AN EFFICIENT SYNTHESIS OF ALPHA-KETO ACIDS, ESTERS, AND AMIDES

Authors
WASSERMAN HH HO WB
Citation
Hh. Wasserman et Wb. Ho, (CYANOMETHYLENE)PHOSPHORANES AS NOVEL CARBONYL 1,1-DIPOLE SYNTHONS - AN EFFICIENT SYNTHESIS OF ALPHA-KETO ACIDS, ESTERS, AND AMIDES, Journal of organic chemistry, 59(16), 1994, pp. 4364-4366
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
16
Year of publication
1994
Pages
4364 - 4366
Database
ISI
SICI code
0022-3263(1994)59:16<4364:(ANC1S>2.0.ZU;2-H
Abstract
Carboxylic acids react with (cyanomethylene)triphenylphosphorane in th e presence of EDCI to form cyano keto phosphoranes. The resulting ylid es may then be oxidatively cleaved with ozone to form alpha,beta-diket onitriles. These highly electrophilic products may then be converted i n situ to alpha-keto acids, esters, and amides.