Issue 24, 2022

Palladium-catalyzed aza-Wacker cyclization of O-homoallyl benzimidates: expeditious access to heteroatom-rich substituted 1,3-oxazines via alkene trifunctionalization

Abstract

A palladium-catalyzed aza-Wacker cyclization of O-homoallyl benzimidates has been developed to afford a variety of useful 4-methylene-1,3-oxazine building blocks in moderate to good yields. The synthetic utility of the 4-methylene-1,3-oxazines is illustrated by the conversion of the exo C[double bond, length as m-dash]C bond to a diverse collection of heteroatom-rich moieties through subsequent electrophilic addition enabling C–I, C–Br, C–Cl, C–O, C–N, and C–C bond formations. These tandem protocols scale well, and their products are demonstrated to be valuable frameworks for use in medicinal and biological chemistry.

Graphical abstract: Palladium-catalyzed aza-Wacker cyclization of O-homoallyl benzimidates: expeditious access to heteroatom-rich substituted 1,3-oxazines via alkene trifunctionalization

Supplementary files

Article information

Article type
Research Article
Submitted
01 Aug 2022
Accepted
06 Nov 2022
First published
07 Nov 2022

Org. Chem. Front., 2022,9, 6909-6914

Palladium-catalyzed aza-Wacker cyclization of O-homoallyl benzimidates: expeditious access to heteroatom-rich substituted 1,3-oxazines via alkene trifunctionalization

L. Zhang, L. Qi, H. Du, J. Liu, T. Cao, Z. Yan, W. Li and L. Wang, Org. Chem. Front., 2022, 9, 6909 DOI: 10.1039/D2QO01233B

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