Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes

The work in this thesis was undertaken in Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences in Nanyang Technological University from January 2010 to March 2014 under the supervision of Prof. Philip Wai Hong Chan. The work of this thesis has been directed towards establ...

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Main Author: Li, Dan
Other Authors: Philip Wai Hong Chan
Format: Thesis
Language:English
Published: 2014
Subjects:
Online Access:https://hdl.handle.net/10356/61787
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author Li, Dan
author2 Philip Wai Hong Chan
author_facet Philip Wai Hong Chan
Li, Dan
author_sort Li, Dan
collection NTU
description The work in this thesis was undertaken in Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences in Nanyang Technological University from January 2010 to March 2014 under the supervision of Prof. Philip Wai Hong Chan. The work of this thesis has been directed towards establishing gold-catalyzed intramolecular cyclization as novel synthetic strategies to carbocycles. This thesis is divided into three parts:  Part I consists of Chapter I, which gives an introduction to gold catalysis and its application in the cycloisomerization of 1,n-enyne esters and 1,n-diyne carbonates and esters.  Part II is aimed at exploring novel gold-catalyzed cyclization of 1,n-diyne esters and carbonates for the preparation of synthetically useful cyclic organic compounds. Chapter II addresses an efficient gold-catalyzed, expedient and chemoselective approach for the transformation of 1,6-diyne carbonates and esters to 2,4a-dihydro-1H-fluorenes which could be found in a lot of natural and synthetic compounds and functional materials. Chapter III describes an efficient gold-catalyzed cyclization strategy to structurally diverse 1H-cyclopenta[b]naphthalenes, cyclopenten-2-yl δ-ciketones and bicyclo[3.2.0]hepta-1,5-dienes.  Part III contains the experimental data (Chapter V) and references (Chapter VI) pertaining to this thesis.
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spelling ntu-10356/617872023-02-28T23:37:52Z Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes Li, Dan Philip Wai Hong Chan School of Physical and Mathematical Sciences DRNTU::Science::Biological sciences::Biochemistry The work in this thesis was undertaken in Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences in Nanyang Technological University from January 2010 to March 2014 under the supervision of Prof. Philip Wai Hong Chan. The work of this thesis has been directed towards establishing gold-catalyzed intramolecular cyclization as novel synthetic strategies to carbocycles. This thesis is divided into three parts:  Part I consists of Chapter I, which gives an introduction to gold catalysis and its application in the cycloisomerization of 1,n-enyne esters and 1,n-diyne carbonates and esters.  Part II is aimed at exploring novel gold-catalyzed cyclization of 1,n-diyne esters and carbonates for the preparation of synthetically useful cyclic organic compounds. Chapter II addresses an efficient gold-catalyzed, expedient and chemoselective approach for the transformation of 1,6-diyne carbonates and esters to 2,4a-dihydro-1H-fluorenes which could be found in a lot of natural and synthetic compounds and functional materials. Chapter III describes an efficient gold-catalyzed cyclization strategy to structurally diverse 1H-cyclopenta[b]naphthalenes, cyclopenten-2-yl δ-ciketones and bicyclo[3.2.0]hepta-1,5-dienes.  Part III contains the experimental data (Chapter V) and references (Chapter VI) pertaining to this thesis. DOCTOR OF PHILOSOPHY (SPMS) 2014-10-09T09:04:42Z 2014-10-09T09:04:42Z 2014 2014 Thesis Li, D. (2014). Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/61787 10.32657/10356/61787 en 166 p. application/pdf
spellingShingle DRNTU::Science::Biological sciences::Biochemistry
Li, Dan
Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title_full Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title_fullStr Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title_full_unstemmed Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title_short Gold-catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
title_sort gold catalyzed cycloisomerization strategies for the stereoselective synthesis of carbocycles from alkynes
topic DRNTU::Science::Biological sciences::Biochemistry
url https://hdl.handle.net/10356/61787
work_keys_str_mv AT lidan goldcatalyzedcycloisomerizationstrategiesforthestereoselectivesynthesisofcarbocyclesfromalkynes