Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst

…, JS Parratt, NJ Turner, J Crosby, J Moilliet

Index: Beard, Timothy; Cohen, Mark A.; Parratt, Julian S.; Turner, Nicholas J.; Crosby, John; Moilliet, Jock Tetrahedron: Asymmetry, 1993 , vol. 4, # 6 p. 1085 - 1104

Full Text: HTML

Citation Number: 69

Abstract

Abstract An immobilised whole cell Rhodococcus sp.(SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R) amides whereas the closely related substrate 9a gave the (R)-acid. A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with ee's 22–84%. ...