| Summary: | The work in this thesis was undertaken at the Division of Chemistry and
Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang
Technological University from August 2008 to June 2012 under the supervision of
Asst. Prof. Philip Wai Hong Chan.
The work of this thesis has been directed toward establishing new Lewis and
Brønsted acid-catalyzed reactions of alcohol pro-electrophiles as novel synthetic
strategies for C−X (X = C, N, O, S) bond formation. This thesis is divided into three
parts:
Part I consists of Chapter I, which gives an introduction of Lewis and
Brønsted acid catalyzed reactions of alcohol pro-electrophiles, particularly
those containing a pendant activated alcohols such as allylic, propargylic,
benzylic and cyclopropylmethyl functional group.
Part II describes the new strategies developed for C−X (X = C, N, O) bond
formation employing alcohols as pro-electrophiles. Chapter II addressed
highly efficient synthesis of tri- and tetrasubstituted conjugated enynes from
Brønsted acid catalyzed alkoxylation of 1-cyclopropylprop-2-yn-1-ols with
alcohols. In Chapter III, a novel strategy to halohydrofurans via Brønsted
acid-catalyzed hydroxylation/halocyclization of cyclopropyl methanols with
water and electrophilic halides is described. Chapter IV represented the silver
triflate-catalyzed tandem heterocyclization/alkynylation of
1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles. In Chapter V,
a new method to tri- and tetrasubstituted furans via Brønsted acid-catalyzed
cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl
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compounds is disclosed. Chapter VI detailed silver-catalyzed tandem
amination/spiro annulation of 1-(2-(allylamino)phenyl)-4-hydroxy-but-2-yn-
-1-ones as an expedient approach to 1'-allylspiro[indene-1,2'-indolin]-3'-ones.
Part III contains the experimental section (Chapter VII) and references section
(Chapter VIII) pertaining to this thesis.
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