A CONVENIENT ACCESS TO N,N-DISUBSTITUTED AMIDES DERIVED FROM 3S)-2,2-DIMETHYL-3-FORMYLCYCLOPROPANE-1-CARBOXYLIC ACID

Authors
PEROLLIER C PECAUT J RAMASSEUL R MARCHON JC
Citation
C. Perollier et al., A CONVENIENT ACCESS TO N,N-DISUBSTITUTED AMIDES DERIVED FROM 3S)-2,2-DIMETHYL-3-FORMYLCYCLOPROPANE-1-CARBOXYLIC ACID, Bulletin de la Societe chimique de France, 134(5), 1997, pp. 517-523
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
134
Issue
5
Year of publication
1997
Pages
517 - 523
Database
ISI
SICI code
0037-8968(1997)134:5<517:ACATNA>2.0.ZU;2-6
Abstract
Enantiopure N,N-disubstituted amides are obtained in good yield from ( -)-2,2-dimethyl-3-formylcyclopropane-1-carboxylic acid in three steps: dithiane protection of the aldehyde function; amidation of the carbox ylic acid function; dethioketalization. Mono-N-substituted amides rear range to a bicyclic lactam form. The X-ray structure of a dithiane-pro tected mono-N-substituted amide intermediate is reported.