Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio- and stereoselective hydroxylation with Sphingomonas sp. HXN-200.
[reaction: see text] Enantiopure (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones have been prepared for the first time by regio- and stereoselective hydroxylation of the corresponding pyrrolidin-2-ones by use of a biocatalyst. Hydroxylation of 6 and 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.
Chang
D
D
Institute of Biotechnology, ETH-Zurich, Honggerberg, CH-8093 Zurich, Switzerland.
Witholt
B
B
Li
Z
Z
D002851:Chromatography, High Pressure Liquid; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000737:chemistry / Q000378:metabolism*; D020578:Sphingomonas / Q000378:metabolism*; D013237:Stereoisomerism
D011759:Pyrrolidines