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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.