Synthesis of enantiomerically enriched Baylis-Hillman alcohols from their acetates:: combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate

Enantiomerically enriched Baylis-Hillman alcohols 2a-d (S) were prepared in 25-42% yields with optical purities of 54-92% ee by using the combined concept of kinetic resolution during the salt formation of racemic Baylis-Hillman acetates 1a-d with (DHQD)(2)PHAL and the asymmetric induction during the S(N)2' type reaction with sodium bicarbonate as a water surrogate. (C) 2002 Elsevier Science Ltd. All rights reserved.