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

Nie Lei | Zendy; Yang Rui | Zendy; Zhang Conghai | Zendy; Yin Haichuan | Zendy; Yan Shengjiao | Zendy; Lin Jun | Zendy

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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

Author(s) -

Nie Lei,

Yang Rui,

Zhang Conghai,

Yin Haichuan,

Yan Shengjiao,

Lin Jun

Publication year - 2012

Publication title -

chinese journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.28

H-Index - 41

eISSN - 1614-7065

pISSN - 1001-604X

DOI - 10.1002/cjoc.201180489

Subject(s) - chemistry , furan , stereoselectivity , hydrolysis , amino acid , acid hydrolysis , stereochemistry , organic chemistry , medicinal chemistry , catalysis , biochemistry

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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