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

All four isomers of a novel fl-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 a...

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Veröffentlicht in:Chinese journal of chemistry 2012-02, Vol.30 (2), p.460-465
1. Verfasser: Nie, Lei Yang, Rui Zhang, Conghai Yin, Haichuan Yan, Shengjiao Lin, Jun
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Sprache:eng
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Zusammenfassung:All four isomers of a novel fl-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.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201180489