Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids

Tyler J. Fulton, Alexander Q. Cusumano, Eric J. Alexy, Yun E. Du, Haiming Zhang, K. N. Houk* and Brian M. Stoltz*

*University of California, Los Angeles, California 90095; California Institute of Technology, Pasadena, California 91125, United States, Email: houkchem.ucla.edu, stoltzcaltech.edu

T. J. Fulton, A. Q. Cusumano, E. J. Alexy, Y. E. Du, H Zhang, K. N. Houk, B. M. Stoltz, J. Am. Chem. Soc., 2020, 142, 21938-21947.

DOI: 10.1021/jacs.0c11480

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Abstract

The Ireland-Claisen rearrangement of tetrasubstituted α-phthalimido ester enolates affords α-tetrasubstituted, β-trisubstituted α-amino acids (generally >20:1 dr). The diastereochemical outcome of the reaction is preserved regardless of the geometry of the enolate or the accompanying allylic olefin.

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stereoconvergent Ireland-Claisen Rearrangement

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Key Words

Ireland-Claisen Rearrangement, α-Amino Acids

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ID: J48-Y2020