Visible light-mediated cyclizations of cyclic enones

<p>The work outlined in this thesis covers the development of visible light-mediated cyclizations of cyclic enones. Chapter one provides an overview of photochemical cyclizations, focusing on visible light-mediated cyclizations using triplet energy transfer from a suitable sensitizer, as well...

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Main Author: Parker, NA
Other Authors: Smith, M
Format: Thesis
Language:English
Published: 2020
Subjects:
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author Parker, NA
author2 Smith, M
author_facet Smith, M
Parker, NA
author_sort Parker, NA
collection OXFORD
description <p>The work outlined in this thesis covers the development of visible light-mediated cyclizations of cyclic enones. Chapter one provides an overview of photochemical cyclizations, focusing on visible light-mediated cyclizations using triplet energy transfer from a suitable sensitizer, as well as an overview of the photochemical cyclizations of cyclic enones. Chapter two discusses the development of a visible light-mediated intramolecular arylation of cyclic 2-arylheteroenones to generate a wide range of cis-fused heterocycles.</p> <p>Chapter three details efforts into the photochemical synthesis of spirocyclic compounds via intramolecular hydrogen atom abstraction using a cyclic enone chromophore. Chapter four discusses the development of a visible light-mediated spirocyclization of cyclic 2-amidoenones. After initial optimization, the scope and scalability of the reaction was explored, and derivatization of the products investigated. Subsequent mechanistic experiments provided insight into the high diastereoselectivity of the reaction.</p> <p>Chapter five looks at applications of the previously developed reactions to acyclic chromophore systems, and the challenges present in this modification </p>
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spelling oxford-uuid:0af487c1-fdd0-4292-890d-61f6a05c21492024-12-01T11:28:30ZVisible light-mediated cyclizations of cyclic enonesThesishttp://purl.org/coar/resource_type/c_db06uuid:0af487c1-fdd0-4292-890d-61f6a05c2149Organic ChemistryPhotochemistryEnglishORA Deposit2020Parker, NASmith, M<p>The work outlined in this thesis covers the development of visible light-mediated cyclizations of cyclic enones. Chapter one provides an overview of photochemical cyclizations, focusing on visible light-mediated cyclizations using triplet energy transfer from a suitable sensitizer, as well as an overview of the photochemical cyclizations of cyclic enones. Chapter two discusses the development of a visible light-mediated intramolecular arylation of cyclic 2-arylheteroenones to generate a wide range of cis-fused heterocycles.</p> <p>Chapter three details efforts into the photochemical synthesis of spirocyclic compounds via intramolecular hydrogen atom abstraction using a cyclic enone chromophore. Chapter four discusses the development of a visible light-mediated spirocyclization of cyclic 2-amidoenones. After initial optimization, the scope and scalability of the reaction was explored, and derivatization of the products investigated. Subsequent mechanistic experiments provided insight into the high diastereoselectivity of the reaction.</p> <p>Chapter five looks at applications of the previously developed reactions to acyclic chromophore systems, and the challenges present in this modification </p>
spellingShingle Organic Chemistry
Photochemistry
Parker, NA
Visible light-mediated cyclizations of cyclic enones
title Visible light-mediated cyclizations of cyclic enones
title_full Visible light-mediated cyclizations of cyclic enones
title_fullStr Visible light-mediated cyclizations of cyclic enones
title_full_unstemmed Visible light-mediated cyclizations of cyclic enones
title_short Visible light-mediated cyclizations of cyclic enones
title_sort visible light mediated cyclizations of cyclic enones
topic Organic Chemistry
Photochemistry
work_keys_str_mv AT parkerna visiblelightmediatedcyclizationsofcyclicenones