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Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds

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Abstract

β-Di-substituted α-amino acids (AAs) contain adjacent carbon stereogenic centers and pose considerable synthetic challenge. Complementary to the conventional synthesis strategies based on the transformation of existing functional groups, we envisioned these molecules could be quickly accessed via selective functionalization of sp3 hybridized C-H bonds on the side chains of common α-AA precursors. We report a readily applicable method to prepare β-alkynyl α-amino acids via Pd-catalyzed diastereoselective C(sp3)-H alkynylation of common α-amino acids precursors with acetylene bromide.

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  30. It should be noted that alkylation using other alkynyl halide coupling partners gave significantly lower yield.

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Authors and Affiliations

  1. Department of Chemistry, the Pennsylvania State University, University Park, Pennsylvania, 16802, USA

    Bo Wang, Gang He & Gong Chen

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  1. Bo Wang
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  2. Gang He
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  3. Gong Chen
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Correspondence to Gong Chen.

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Wang, B., He, G. & Chen, G. Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds. Sci. China Chem. 58, 1345–1348 (2015). https://doi.org/10.1007/s11426-015-5392-z

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