Nucleophilic Addition of 4,5-Dihydrooxazole Derivatives to Base Generated o-Quinone Methides: A Four-Component Reaction

J Org Chem. 2023 Feb 17;88(4):2583-2588. doi: 10.1021/acs.joc.2c02614. Epub 2023 Jan 31.

Abstract

A novel method for joining four components together in a single pot leading to an assortment of N-amino-benzylated phenols is described. The method involves the addition of different Grignard reagents to various o-OBoc salicylaldehydes in the presence of assorted 4,5-dihydrooxazoles, followed by aqueous workup. Seventeen examples are presented with varied (-R, -R' -R″, -R‴, -R⁗, and Cn) substituents.