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

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.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2018

Author dc:creator

• Young, Jonathon Michael

Contributors dc:contributor

• White, Maria C.

• C—H activation, organometallics

Statement dc:rights

• Copyright 2018 Jonathon Young

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/101375

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/101375