A novel modification of the Ritter reaction: stereoselective synthesis of bridgehead-fused Δ2-norbornanethiazolines from thiocamphor and thiofenchone

García Martínez, Antonio; Teso Vilar, Enrique; Moreno Jiménez, Florencio; Álvarez García, Ana María

A novel modification of the Ritter reaction: stereoselective synthesis of bridgehead-fused Δ2-norbornanethiazolines from thiocamphor and thiofenchone

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Official URL

https://doi.org/10.1016/j.tetasy.2006.11.003

Publication date

2006

Authors

García Martínez, Antonio

Teso Vilar, Enrique

Moreno Jiménez, Florencio

Álvarez García, Ana María

Publisher

Elsevier

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URI

https://hdl.handle.net/20.500.14352/52834

Abstract

An easy two-step route for the stereoselective synthesis of novel bridgehead-fused norbornanethiazolines from readily available natural camphor and fenchone is described. The key step of the synthetic route is the highly stereoselective trapping of 1-(trifluoromethylsulfonylthio)-2-norbornyl cations by nitriles followed by intramolecular cyclization, which constitutes a new modification of the Ritter reaction

Description

Received 18 September 2006, Accepted 2 November 2006, Available online 1 December 2006.