Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio-and stereoselective hydroxylation with Sphingomonas sp HXN-200

Authors
Chang, DL Witholt, B Li, Z
Citation
Dl. Chang et al., Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio-and stereoselective hydroxylation with Sphingomonas sp HXN-200, ORG LETT, 2(24), 2000, pp. 3949-3952
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
24
Year of publication
2000
Pages
3949 - 3952
Database
ISI
SICI code
1523-7060(20001130)2:24<3949:PO(4BR>2.0.ZU;2-K
Abstract
Enantiopure (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones have been prepare d for the first time by regio- and stereoselective hydroxylation of the cor responding pyrrolidin-2-ones by use of a biocatalyst. Hydroxylation of 6 an d 8 with Sphingomonas sp. HXN-200 afforded 68% of (S)-7 in >99.9% ee and 46 % of (S)-9 in 92% ee, respectively. Simple crystallization increased the ee of (S)-9 to 99.9% in 82% yield.