Copper chloride-catalyzed and hydrochloric acid-mediated chemoselective protiodestannylations of alkyl (Z)- or (E)-2,3-Bis(trimethylstannyl)-2-alkenoates. Stereoselective preparation of alkyl (E)- and (Z)-3-trimethylstannyl-2-alkenoates

摘要

Treatment of alkyl (Z)-2,3-bis(riethylstannyl)-2-alkenoates (7)with a catalytic amount of copper(I) chloride in N,N-dimethylformatide (DMF) containing a small quantity of water provides very good- to-excellent yields of alkyl (E)-3-triethylstannyl-2-alkenoates (1). On the other hand, stirring of solutions of alkyl (Z)- (7) or (E)-2-3-bis(trimethylstannyl)-2-alkenotes (8) in DMF containing dilute hydrochloric acid produces, efficiently, alkyl (Z)-3-trimethylstannyl-2-alkenoates (2).