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Asymmetric Synthesis of All Four Isomers of an Unusual Heterocycle-Containing Amino Acid: 2-Amino-3-furan-2-yl-pentanoic Acid

  1. Lei Nie1,
  2. Rui Yang1,
  3. Conghai Zhang1,
  4. Haichuan Yin2,
  5. Shengjiao Yan1,
  6. Jun Lin1,*

Article first published online: 15 FEB 2012

DOI: 10.1002/cjoc.201180489

Issue

Chinese Journal of Chemistry

Chinese Journal of Chemistry

Volume 30, Issue 2, pages 460–465, February, 2012

Additional Information

How to Cite

Nie, L., Yang, R., Zhang, C., Yin, H., Yan, S. and Lin, J. (2012), Asymmetric Synthesis of All Four Isomers of an Unusual Heterocycle-Containing Amino Acid: 2-Amino-3-furan-2-yl-pentanoic Acid. Chin. J. Chem., 30: 460–465. doi: 10.1002/cjoc.201180489

Author Information

  1. 1

    Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China

  2. 2

    The Education Department of Yunnan Province, Kunming, Yunnan 650091, China

*Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China

Publication History

  1. Issue published online: 15 FEB 2012
  2. Article first published online: 15 FEB 2012
  3. Manuscript Accepted: 25 AUG 2011
  4. Manuscript Received: 24 MAR 2011

Funded by

  • the National Natural Science Foundation of China. Grant Number: 20472071, 20562014 and 30860342
  • Natural Science Foundation of Yunnan Province. Grant Number: 2009cc017

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Keywords:

  • asymmetric synthesis;
  • unusual amino acid;
  • oxazolidinone;
  • chiral auxiliary;
  • 2-amino-3-furan-2-yl- pentanoic acid

Abstract

All four isomers of a novel β-branched unusual amino acid were designed and synthesized with high stereoselectivity (>90% de) and in 33% –44% overall yields by the use of 4(R/S)-5,5-dimethyl-4-phenyl-oxazolidin-2-one as the chiral auxiliary via asymmetric 1,4-Michael addition, direct or indirect azidation, hydrolysis and hydrogenation reactions.

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