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

✍ Scribed by Jae Nyoung Kim; Hong Jung Lee; Ji Hyeon Gong

• Book ID: 104252431
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 508 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02274-8

✦ Synopsis

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.