Study of the Reduction of Enamides with an NADH Model

✍ Scribed by Corine Leroy; Vincent Levacher; Georges Dupas; Jean Bourguignon; Guy Quéguiner

• Book ID: 104224755
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 250 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91687-3

✦ Synopsis

Abslract : The regioselectivity of the reduction of the cyclic enamide 2a with an NADH model compound was established using a deuterated model. The geometry of the substrate seems to play a fundamental role since cyclic derivatives 2a and 2d were reduced and non cyclic derivatives 2b and 2c were not reduced. Electronic factors were also examined.

Enamides (N-acylenamines) are successfully reduced by catalytic hydrogenation 1. There is only one example to our knowledge where an enamide was reduced with an hydride donor 2 .

In a recent paper we reported the successful reduction of the carbon-carbon double bond of the tertiary enamide 2a with an NADH model la 3 leading, after proper transformations, to racemic salsolidine.