Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 347, Issue 11-13, Pages 1701-1708Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505230
Keywords
asymmetric catalysis; aza-Baylis-Hillman reaction; kinetic isotope effect; organocatalysis; thiourea catalyst
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We report the discovery of asymmetric aza-Baylis-Hillman (ABH) reactions of N-p-nitrobenzenesulfonylimines with methyl acrylate catalyzed by chiral thiourea derivatives. A series of aromatic imines was found to undergo coupling with methyl acrylate with unprecedented levels of enantioselectivity (87-99% ee), albeit only in modest (25-49%) yields. A DABCO-acrylate-imine adduct was isolated as a key intermediate in the ABH reaction. We provide a mechanistic analysis based on the identity of this intermediate as well as kinetic investigations and isotope studies, and propose a rationale for the observed limitations in yield. Synthetic applications of the ABH products are also described.
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