| Summary: | The work in this thesis is described in two sections. In the first section, the conjugate
addition of alkenyltrirnethylstannane functions to α,β-alkynic esters mediated by copper(I)
chloride are discussed. An experimental protocol employing copper(I) chloride and acetic acid
in N,N-dimethylforaiamide was developed to effect the stereoselective conversion of the
precursors 80 and 178-185 into the monocyclic compounds 81 and bicyclic compounds 186-193,
respectively. The intramolecular copper(I)-mediated conjugate addition of aryltrimethyl
stannane functions to α,β -alkynic esters was also explored. A variety of bicyclic compounds of
general structure 89 that each incorporate an aromatic ring were prepared by this method.
α,β -Alkynic aldehydes and α,β -alkynic ketones were shown to function as viable Michael
acceptors in the conversion of 233 and 235 into 236-237 and 238-239, respectively. The
catalytic nature of the copper(I) chloride in the reaction was also demonstrated.
In the second part of this thesis, the copper(I) chloride-mediated oxidative coupling of
alkenyltrimethylstannane and aryltrimethylstannane functions is discussed. The intermolecular
homocoupling of β-trirnethylstannyl- α,β -unsaturated ketones 100 produced the structurally
unusual diketones 101 upon the treatment of the precursors with copper(I) chloride. The
synthesis of the 5-, 6-, and 7-membered ring compounds 105, 107, 109, 111, and 113 from the
precursors 104, 106, 108, 110, and 112, respectively, was accomplished by use of the
intramolecular variant of the coupling reaction. The scope of the methodology was extended to
include the formation of 9-membered and 10-membered ring compounds of general structure
115. === Science, Faculty of === Chemistry, Department of === Graduate
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