Syntheses and Configuration Inversion of Substituted Oxazolines

Chemical Research in Chinese Universities ›› 2001, Vol. 17 ›› Issue (3): 271-275.

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Syntheses and Configuration Inversion of Substituted Oxazolines

YANG Shao-rong, HU Quan-yuan, LIU Jun, YANG Hui, HU Xian-ming

College of Chemistry, Wuhan University, Wuhan 430072, P. R. China

Received:2000-03-31 Online:2001-08-24 Published:2011-08-04
Supported by:
Supported by the Science and Technology Fundation of Wuhan City and Wuhan Red Heart K(Group) Co. Ltd.

Abstract

Abstract: The present paper covers the simply and highly stereoselective syntheses of (α-S, 4S)-2-dichloromethyl- 4, 5-dihydro-α- (4-nitrophenyl)- 4-oxazolemethanol (4a), (α-S,4S)-2-methyl-4,5-dihydro-α- (4-nitrophenyl)-4-oxazolemethanol (4b), and (α-R, 4R)-2-dichloromethyl-4,5-di-hydro-α- [ (4-methylsulfonyl) phenyl] - 4 -oxazolemethanol (4c) with good yields (80 % - 900%).A configuration inversion product, (1R, 2S)-2-dichloroacetamido-1-(4-nitrophenyl)-1, 3-propane-diol (8), was obtained during our attempting to convert compound 4a into (4S, 5R)-2-(dichloromethyl)-4,5-dihydro-5- (4-nitrophenyl)-4-oxazolemethanol(7).

Key words: Oxazoline, Heterocyclic, Configuration inversion

YANG Shao-rong, HU Quan-yuan, LIU Jun, YANG Hui, HU Xian-ming. Syntheses and Configuration Inversion of Substituted Oxazolines[J]. Chemical Research in Chinese Universities, 2001, 17(3): 271-275.

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Syntheses and Configuration Inversion of Substituted Oxazolines

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