A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions

ABSTRACT: Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1,1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of th...

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Detalles Bibliográficos
Autores principales: Waser, Mario, Haunschmidt, Manuela, Himmelsbach, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2010
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4202191/
https://www.ncbi.nlm.nih.gov/pubmed/25339780
http://dx.doi.org/10.1007/s00706-010-0410-5
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author Waser, Mario
Haunschmidt, Manuela
Himmelsbach, Markus
author_facet Waser, Mario
Haunschmidt, Manuela
Himmelsbach, Markus
author_sort Waser, Mario
collection PubMed
description ABSTRACT: Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1,1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of this reaction. Supported by force field calculations, the high sensitivity of this intermediate was judged to be due to the formation of a highly strained trans-configured bicyclo[3.3.0]skeleton. GRAPHICAL ABSTRACT: [Image: see text]
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spelling pubmed-42021912014-10-20 A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions Waser, Mario Haunschmidt, Manuela Himmelsbach, Markus Monatsh Chem Original Paper ABSTRACT: Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1,1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of this reaction. Supported by force field calculations, the high sensitivity of this intermediate was judged to be due to the formation of a highly strained trans-configured bicyclo[3.3.0]skeleton. GRAPHICAL ABSTRACT: [Image: see text] Springer Vienna 2010-10-30 2010 /pmc/articles/PMC4202191/ /pubmed/25339780 http://dx.doi.org/10.1007/s00706-010-0410-5 Text en © Springer-Verlag 2010
spellingShingle Original Paper
Waser, Mario
Haunschmidt, Manuela
Himmelsbach, Markus
A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title_full A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title_fullStr A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title_full_unstemmed A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title_short A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
title_sort remarkable cyclization of taddol-bisthioacetate under oxidative conditions
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4202191/
https://www.ncbi.nlm.nih.gov/pubmed/25339780
http://dx.doi.org/10.1007/s00706-010-0410-5
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