Enantioselective Synthesis of anti-β-Substituted γ,δ-Unsaturated Amino Acids: A Highly Selective Asymmetric Thio-Claisen Rearrangement

作者: Zhihua Liu , Hongchang Qu , Xuyuan Gu , Byoung J. Min , Joel Nyberg

DOI: 10.1021/OL801657Q

关键词: ChemistryEnantioselective synthesisAmino acidClaisen rearrangementThio-Chiral auxiliarySulfurStereochemistryHighly selectiveStereoisomerism

摘要: A novel synthesis of optically active anti-1β-substituted γ,δ-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. 2,5-diphenylpyrrolidine was used as C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities enantioselectivities.

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