Synlett 2006(19): 3275-3276  
DOI: 10.1055/s-2006-951543
LETTER
© Georg Thieme Verlag Stuttgart · New York

Catalytic Acylcyanation of Imines with Acetylcyanide

Subhas Chandra Pan, Jian Zhou, Benjamin List*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062999; e-Mail: list@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 15 August 2006
Publication Date:
23 November 2006 (online)

Abstract

Aldimines react with acetyl cyanide in the presence of a catalytic amount of a thiourea catalyst to give the corresponding N-acetylated amino nitriles in high yields. The scope of the reaction is broad and both aromatic as well as aliphatic aldimines can readily be used.

6

Under our reaction conditions using triethylamine as the catalyst only 4% conversion of imine 1a to product 4a was achieved.

9

Even in the absence of catalyst, significant conversion (>30%) to the product was observed.

10

Using the chiral phosphoric acid catalyst 3,3′-bis[(2,4,6-tris(isopropyl)phenyl]-5,5′,6,6′,7,7′,8,8′-octahydro-1,1-binaphthyl hydrogen phosphate (10 mol%) at -40 °C, product 4a was obtained in 92% yield and 69:31 er.