Asymmetric Synthesis of All Four Isomers of an Unusual Heterocycle‐Containing Amino Acid: 2‐Amino‐3‐furan‐2‐yl‐pentanoic Acid |
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| Authors: | Lei Nie Rui Yang Conghai Zhang Haichuan Yin Shengjiao Yan Jun Lin |
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| Institution: | 1. Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China;2. The Education Department of Yunnan Province, Kunming, Yunnan 650091, China |
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| 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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| Keywords: | asymmetric synthesis unusual amino acid oxazolidinone chiral auxiliary 2‐amino‐3‐furan‐2‐yl‐ pentanoic acid |
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