Gold-catalyzed strategies for carbocyclic and n-heterocyclic synthesis

Abstract

The work in this thesis was undertaken in Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences in Nanyang Technological University from August 2010 to August 2014 under the supervision of Assoc. Prof. Philip Wai Hong Chan. In this thesis the development of several novel gold-catalyzed transformations for the construction of carbocycles and N-heterocycles via C–C and C–N bond formation are described. This thesis consists of three parts: 􀂾? Part I includes Chapter I, which gives the general introduction of gold catalysis and its application for the construction carbocycles and N-heterocycles from readily available alkynols and 1,n-diyne esters.􀂾? Part II describes the new strategies that have been employed to access sulfonyl pyrroles, phenolic esters and bicyclo[2.2.1]hept-2-en-7-one derivatives. Chapter II presents gold-mediated tandem aminocyclization/1,3-sulfonyl migration of α-amino propargyl alcohols as a new synthetic tool for the preparation of 3-sulfonyl pyrroles. In Chapter III, a synthetic protocol for synthesizing the phenolic esters from the benzannulation of gold(I)-activated parpargylic alcohol tethered β-ketoesters is introduced. This method features its reaction conditions that did not require the exclusion of air or moisture. Chapter IV details a novel synthetic route to bicyclo[2.2.1]hept-2-en-7-one derivatives based on acyloxy migration followed by enyne cycloisomerization of 1,8-diynyl vinyl esters. 􀂾? Part III contains experimental data (Chapter V) and references (Chapter VI) pertaining to this thesis.