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

Authors
Takabe, K Suzuki, M Nishi, T Hiyoshi, M Takamori, Y Yoda, H Mase, N
Citation
K. Takabe et al., 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, TETRAHEDR L, 41(50), 2000, pp. 9859-9863
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
50
Year of publication
2000
Pages
9859 - 9863
Database
ISI
SICI code
0040-4039(200012)41:50<9859:CRTBEO>2.0.ZU;2-Z
Abstract
High enantioselectivity was achieved in the lipase-catalyzed kinetic resolu tion of 5-hydroxypyrrolidin-2-one and 5-hydroxy-1,5-dihydropyrrol-2-one der ivatives. Lipase PS and Novozym 435 were the successful catalysts (E = >100 0), The acetylation of the N-protected 5-hydroxy-1,5-dihydropyrrol-2-one de rivative gave the (R)-acetate with high enantioselectivity, while, without N-protection, the (S)-acetate was obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.