Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides

J Org Chem. 2019 Nov 1;84(21):14258-14269. doi: 10.1021/acs.joc.9b02040. Epub 2019 Oct 23.

Abstract

A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the cases.

Publication types

  • Research Support, Non-U.S. Gov't