Asymmetric Eschenmoser-Claisen rearrangement for anti-beta-substituted gamma,delta-unsaturated amino acids |
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Authors: | Qu Hongchang Gu Xuyuan Liu Zhihua Min Byoung J Hruby Victor J |
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Institution: | Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA. |
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Abstract: | Optically active anti-beta-substituted gamma,delta-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction. |
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