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Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides

Barry M. Trost* , James J. Cregg and Nicolas Quach

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States, Email: bmtroststanford.edu

B. M. Trost, J. J. Cregg, N. Quach, J. Am. Chem. Soc., 2017, 139, 5133-5139.

DOI: 10.1021/jacs.7b00564 (free Supporting Information)


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Abstract

A general atom economic method for the isomerization of a broad range of N-allyl amides enables the synthesis of Z-di-, tri-, and tetrasubstituted enamides with exceptional geometric selectivity. Applications of these geometrically defined enamides toward the synthesis of cis vicinal amino alcohols and tetrasubstituted α-borylamido complexes are discussed.

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Key Words

enamides


ID: J48-Y2017