Formation of cyclic sulfonamides via an unusual 8-endo-trig Heck olefination reaction

Johannes E.M.N. Klein; Helge Muller-Bunz; Yannick Ortin; Paul Evans

doi:10.1016/j.tetlet.2008.10.004

Formation of cyclic sulfonamides via an unusual 8-endo-trig Heck olefination reaction

Johannes E.M.N. Klein, Helge Muller-Bunz, Yannick Ortin, Paul Evans

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The synthesis of the novel benz[c]azocines, 11a and 11b was achieved following an 8-endo-trig selective intramolecular Heck reaction. Optimisation of this reaction demonstrated that inclusion of both tetra-n-butylammonium sulfate and water was essential for its success. No products from the corresponding 7-exo-trig process were encountered under these conditions.

Original language	English (US)
Pages (from-to)	7187-7190
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.004
State	Published - Dec 8 2008

Bibliographical note

Funding Information:
We would like to thank UCD for financial support and Dr. Dilip Rai for high resolution mass spectrometry.

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10.1016/j.tetlet.2008.10.004

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abstract = "The synthesis of the novel benz[c]azocines, 11a and 11b was achieved following an 8-endo-trig selective intramolecular Heck reaction. Optimisation of this reaction demonstrated that inclusion of both tetra-n-butylammonium sulfate and water was essential for its success. No products from the corresponding 7-exo-trig process were encountered under these conditions.",

author = "Klein, {Johannes E.M.N.} and Helge Muller-Bunz and Yannick Ortin and Paul Evans",

note = "Funding Information: We would like to thank UCD for financial support and Dr. Dilip Rai for high resolution mass spectrometry. ",

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AU - Klein, Johannes E.M.N.

AU - Muller-Bunz, Helge

AU - Ortin, Yannick

AU - Evans, Paul

N1 - Funding Information: We would like to thank UCD for financial support and Dr. Dilip Rai for high resolution mass spectrometry.

PY - 2008/12/8

Y1 - 2008/12/8

N2 - The synthesis of the novel benz[c]azocines, 11a and 11b was achieved following an 8-endo-trig selective intramolecular Heck reaction. Optimisation of this reaction demonstrated that inclusion of both tetra-n-butylammonium sulfate and water was essential for its success. No products from the corresponding 7-exo-trig process were encountered under these conditions.

AB - The synthesis of the novel benz[c]azocines, 11a and 11b was achieved following an 8-endo-trig selective intramolecular Heck reaction. Optimisation of this reaction demonstrated that inclusion of both tetra-n-butylammonium sulfate and water was essential for its success. No products from the corresponding 7-exo-trig process were encountered under these conditions.

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M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Formation of cyclic sulfonamides via an unusual 8-endo-trig Heck olefination reaction

Abstract

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