Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid

The diverse class of N-containing compounds, which comprises various biologically important natural and unnatural substances with complex molecular architecture, has challenged synthetic chemists to devise imaginative strategies towards their construction. This thesis discusses salient synthetic met...

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Main Author: Wang, Siming
Other Authors: Steve Zhou
Format: Theses and Dissertations
Language:English
Published: 2013
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Online Access:https://hdl.handle.net/10356/53522
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-535222023-02-28T23:55:38Z Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid Wang, Siming Steve Zhou Liu Xuewei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry The diverse class of N-containing compounds, which comprises various biologically important natural and unnatural substances with complex molecular architecture, has challenged synthetic chemists to devise imaginative strategies towards their construction. This thesis discusses salient synthetic methodologies to access N-containing compounds including 4-aminocyclopentenones, cyclopentanone-fused indolines and sialic acid from readily available glycals.By judicious choice of the reaction solvent, an array of 4-aminocyclopentenones or cyclopentanone fused indolines was synthesized from common glycals and secondary arylamines. This novel methodology involves an interrupted Nazarov process in which the cyclopentenyl cation intermediate is captured by water or aryl moieties. In addition, we have developed a methodology that allows facile synthesis of common and uncommon sialic acids. This methodology employs a tandem Rh-catalyzed nitrene insertion and Barbier allylation as the key step. DOCTOR OF PHILOSOPHY (SPMS) 2013-06-04T08:31:47Z 2013-06-04T08:31:47Z 2013 2013 Thesis Wang, S. (2013). Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/53522 10.32657/10356/53522 en 145 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Wang, Siming
Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
description The diverse class of N-containing compounds, which comprises various biologically important natural and unnatural substances with complex molecular architecture, has challenged synthetic chemists to devise imaginative strategies towards their construction. This thesis discusses salient synthetic methodologies to access N-containing compounds including 4-aminocyclopentenones, cyclopentanone-fused indolines and sialic acid from readily available glycals.By judicious choice of the reaction solvent, an array of 4-aminocyclopentenones or cyclopentanone fused indolines was synthesized from common glycals and secondary arylamines. This novel methodology involves an interrupted Nazarov process in which the cyclopentenyl cation intermediate is captured by water or aryl moieties. In addition, we have developed a methodology that allows facile synthesis of common and uncommon sialic acids. This methodology employs a tandem Rh-catalyzed nitrene insertion and Barbier allylation as the key step.
author2 Steve Zhou
author_facet Steve Zhou
Wang, Siming
format Theses and Dissertations
author Wang, Siming
author_sort Wang, Siming
title Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
title_short Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
title_full Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
title_fullStr Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
title_full_unstemmed Diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
title_sort diverse reactivity of glycals with arylamines and sulfonamides : synthesis of 4-aminocyclopentenones, cyclopentanone fused indolines and sialic acid
publishDate 2013
url https://hdl.handle.net/10356/53522
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