Highly regio- and enantioselective organocatalytic conjugate addition of alkyl methyl ketones to a beta-silylmethylene malonate.
(S)-N-(2-pyrrolidinylmethyl)pyrrolidine/trifluoroacetic acid (3:1) combination catalyzed the direct addition of alkyl methyl ketones to beta-dimethyl(phenyl)silylmethylene malonate at the methyl terminal with high yield and excellent regio- and enantioselectivity. The silyl group played crucial roles in regioselection and substrate reactivity.
Chowdhury
Raghunath
R
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400085, India.
Ghosh
Sunil K
SK
D000096:Acetone / Q000737:chemistry; D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry
D007659:Ketones; D008314:Malonates; D023303:Oxazolidinones; D011759:Pyrrolidines; C544844:beta-silylmethylene malonate; C058280:preussin; D000096:Acetone; D000841:Anisomycin