1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: A novel approach to alpha-aryl-beta-enamino esters

Authors
Jiang, N Qu, ZH Wang, JB
Citation
N. Jiang et al., 1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: A novel approach to alpha-aryl-beta-enamino esters, ORG LETT, 3(19), 2001, pp. 2989-2992
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
19
Year of publication
2001
Pages
2989 - 2992
Database
ISI
SICI code
1523-7060(20010920)3:19<2989:1A1MIT>2.0.ZU;2-R
Abstract
[GRAPHICS] N-Tosyl diazoketamines were prepared by addition of the ethyl alpha -diazoa cetate anion to N-sulfonylimines. The diazo decomposition of the diazoketam ines with Rh-2(OAc)(4) complex resulted in aryl migration to give alpha -ar yl-beta -enamino esters in good yields and high stereoselectivity. The effe ct of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A reaction mechanism involving a "bridged" phenonium ion is proposed.