Preparation of (R)-and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio-and stereoselective, and easy …

…, D Chang, WA Duetz, JB van Beilen…

Index: Li; Feiten; Chang; Duetz; Van Beilen; Witholt Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8424 - 8430

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Citation Number: 64

Abstract

Hydroxylation of N-benzylpyrrolidine 8 with resting cells of Sphingomonas sp. HXN-200 gave N-benzyl-3-hydroxypyrrolidine 15 in 53% ee (S) with an activity of 5.8 U/g CDW. By changing the “docking/protecting group” in pyrrolidines, hydroxylation activity and enantioselectivity were further improved and the enantiocomplementary formation of 3- hydroxypyrrolidines was achieved: hydroxylation of N-benzoyl-, N-benzyloxycarbonyl-, N- ...