Organocatalytic Michael addition of aldehydes to a β-silylmethylene malonate to form intermediates for the enantioselective synthesis of hydroxylated valerolactones and piperidines

Article abstract of DOI:10.1016/j.tetasy.2010.10.011

The direct Michael addition of enolizable aldehydes to dimethyl(phenyl) silylmethylene malonate was catalysed by an (S)-diphenylprolinol trimethylsilyl ether/acetic acid combination. The adducts were formed in good yield, high diastereoselectivity and excellent enantioselectivity. Chiral valerolactone and piperidine skeletons embedded with a silyl and other functionalities have been made out of the adducts. A total synthesis (+)-simplactone B has been achieved from one of the adducts.