Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis

Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

Detalles Bibliográficos
Autores principales: Zhang, Yan, Vongvilai, Pornrapee, Sakulsombat, Morakot, Fischer, Andreas, Ramström, Olof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498465/
https://www.ncbi.nlm.nih.gov/pubmed/26190961
http://dx.doi.org/10.1002/adsc.201301033
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author Zhang, Yan
Vongvilai, Pornrapee
Sakulsombat, Morakot
Fischer, Andreas
Ramström, Olof
author_facet Zhang, Yan
Vongvilai, Pornrapee
Sakulsombat, Morakot
Fischer, Andreas
Ramström, Olof
author_sort Zhang, Yan
collection PubMed
description Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.
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spelling pubmed-44984652015-07-15 Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis Zhang, Yan Vongvilai, Pornrapee Sakulsombat, Morakot Fischer, Andreas Ramström, Olof Adv Synth Catal Communications Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses. WILEY-VCH Verlag 2014-03-24 2014-03-03 /pmc/articles/PMC4498465/ /pubmed/26190961 http://dx.doi.org/10.1002/adsc.201301033 Text en © 2014 The authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. https://creativecommons.org/licenses/by-nc-nd/4.0/ © 2014 The authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Communications
Zhang, Yan
Vongvilai, Pornrapee
Sakulsombat, Morakot
Fischer, Andreas
Ramström, Olof
Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title_full Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title_fullStr Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title_full_unstemmed Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title_short Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
title_sort asymmetric synthesis of substituted thiolanes through domino thia-michael–henry dynamic covalent systemic resolution using lipase catalysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498465/
https://www.ncbi.nlm.nih.gov/pubmed/26190961
http://dx.doi.org/10.1002/adsc.201301033
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