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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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 |
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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 |
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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. |
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Steve Zhou |
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Steve Zhou Wang, Siming |
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Theses and Dissertations |
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Wang, Siming |
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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 |
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2013 |
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https://hdl.handle.net/10356/53522 |
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1759857507408281600 |