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.
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