Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation
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 d...
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
2012
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| Online Access: | https://hdl.handle.net/10356/50892 |
| _version_ | 1811685342511628288 |
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| author | Srinivasa Reddy Mothe |
| author2 | Chan Philip Wai Hong |
| author_facet | Chan Philip Wai Hong Srinivasa Reddy Mothe |
| author_sort | Srinivasa Reddy Mothe |
| collection | NTU |
| description | 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
vii
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. |
| first_indexed | 2024-10-01T04:43:00Z |
| format | Thesis |
| id | ntu-10356/50892 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:43:00Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | ntu-10356/508922023-02-28T23:41:47Z Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation Srinivasa Reddy Mothe Chan Philip Wai Hong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis 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 vii 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. DOCTOR OF PHILOSOPHY (SPMS) 2012-12-14T07:00:17Z 2012-12-14T07:00:17Z 2012 2012 Thesis Srinivasa, R. M. (2012). Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/50892 10.32657/10356/50892 en 301 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Srinivasa Reddy Mothe Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title | Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title_full | Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title_fullStr | Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title_full_unstemmed | Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title_short | Lewis and Brønsted acid-mediated chemistry of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O) bond formation |
| title_sort | lewis and bronsted acid mediated chemistry of alcohol pro electrophiles as novel synthetic strategies for c x x c n o bond formation |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/50892 |
| work_keys_str_mv | AT srinivasareddymothe lewisandbrønstedacidmediatedchemistryofalcoholproelectrophilesasnovelsyntheticstrategiesforcxxcnobondformation |