S. Masumoto, Masato Suzuki, M. Kanai
Nov 8, 2004
Citations
0
Influential Citations
43
Citations
Journal
Tetrahedron
Abstract
A practical synthesis of (S)-oxybutynin, a muscarinic receptor antagonist, using catalytic enantioselective cyanosilylation of cyclohexyl phenyl ketone (9a) as a key step is described. The key reaction proceeded with 94% ee using 1 mol% of Gd-1 catalyst, and was performed on a 100 g-scale. In addition, a short catalytic enantioselective synthesis of the versatile intermediate for Scios Nova analogues of antimuscarinic agents (7) is described. Application of the catalytic enantioselective cyanosilylation to ketones containing two sterically similar substituents on the carbonyl group is also discussed.