A fast catalytic asymmetric aza-Morita-Baylis-Hiliman reaction of N-sulfonated imines with methyl vinyl ketone in the presence of chiral bifunctional phosphane lewis bases

A series of novel bifunctional chiral phosphane Lewis bases having one phenyl group and an electron-donating alkyl group on the phosphorus atom was designed and successfully synthesized. The use of these bifunctional chiral phosphane Lewis bases in catalytic asymmetric aza-Morita-Baylis-Hillman reactions (aza-MBH reactions) of N-sulfonated imines with methyl vinyl ketone affords the corresponding adducts in good-to-excellent yields and moderate-to-good enantioselectivities within a few hours at room temperature. To the best of our knowledge, this is the fastest catalytic asymmetric MBH reaction reported thus far. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).