Convenient route to both enantiomers of chiral 5-hydroxypyrrolidin-2-one and 5-hydroxy-1,5-dihydropyrrol-2-one: reverse enantioselectivity in lipase-catalyzed kinetic resolution

✍ Scribed by Kunihiko Takabe; Masahisa Suzuki; Toshiki Nishi; Masaomi Hiyoshi; Yasuaki Takamori; Hidemi Yoda; Nobuyuki Mase

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 59 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01745-7

✦ Synopsis

High enantioselectivity was achieved in the lipase-catalyzed kinetic resolution of 5-hydroxypyrrolidin-2one and 5-hydroxy-1,5-dihydropyrrol-2-one derivatives. Lipase PS and Novozym 435 were the successful catalysts (E=>1000). The acetylation of the N-protected 5-hydroxy-1,5-dihydropyrrol-2-one derivative gave the (R)-acetate with high enantioselectivity, while, without N-protection, the (S)-acetate was obtained.