Organocatalytic Michael addition of aldehydes to a β-silylmethylene malonate to form intermediates for the enantioselective synthesis of hydroxylated valerolactones and piperidines
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Add time:09/09/2019 Source:sciencedirect.com
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.
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