Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 17, Pages 3203-3212Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100618
Keywords
Cinchona alkaloids; Michael addition; nitrodienes; organocatalysis; quaternary stereocenter
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Funding
- UGC, India
- DST, India under FIST
- UGC, India, under CAS-I
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A highly regio- and stereoselective protocol for the synthesis of vicinal quaternary and tertiary stereocenters has been developed. The 6'-OH Cinchona alkaloids (BnCPN or BnCPD) at low catalyst loading (0.5-5 mol%) catalyze the Michael addition of trisubstituted carbon nucleophiles to nitrodienes in good to excellent yield (up to > 99), high enantioselectivity (up to 99% ee) and high diastereoselectivity (up to > 99:1 dr) under mild reaction conditions.
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