Allylic C—H activation to access anti-1,3-amino alcohol motifs

Abstract

1,3-Amino alcohols are common motifs in a variety of biologically active molecules including antivirals, antibiotics, antifungals, and various alkaloids. Due to their prevalence and utility as synthetic intermediates, a variety of methods have been developed to access these motifs in a diastereoselective fashion, which are outlined in detail herein.

This thesis documents a novel approach to access anti-1,3-amino alcohols through an intramolecular palladium (II)/sulfoxide-oxazoline catalyzed C—H functionalization between a terminal olefin and an N-tosyl carbamate, generating anti-1,3-oxazinanones. These motifs can be further elaborated upon, making this method ideal for the late stage diversification of complex molecules and pharmaceuticals. This new method can be carried out in the presence of reactive functionality that is not well tolerated by existing methods.