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Title: One-Pot Preparation of Enantiopure Fluorinated β-Amino Acid Precursors: Enantiopure Fluorinated β-Amino Acid Precursors
Award ID(s):
1148295 1461919
NSF-PAR ID:
10017986
Author(s) / Creator(s):
; ;
Date Published:
Journal Name:
European Journal of Organic Chemistry
Volume:
2014
Issue:
24
ISSN:
1434-193X
Page Range / eLocation ID:
5273 to 5280
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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  1. A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ringopening of enantiopure styryl and pyridyl (S)-epoxides by N3  in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl- 2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives. 
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