Radical-mediated 5-exo-trig cyclizations of 3-silylhepta-1,6-dienes

The Journal of Organic Chemistry
Philippe JamesYannick Landais

Abstract

Regioselectivity of the sulfonyl radical mediated 5-exo-trig cyclization of 3-silylheptadienyl systems 3a-d has been studied. At low temperature, the reaction of the sulfonyl radical occurs regioselectively at the allylsilane terminus, while a reversal of regioselectivity is observed at 80 degrees C. This general trend has been rationalized on the basis of polar effects and radical stabilization. Thiyl-mediated radical cyclization of dienes 3a, 3c-d, 7 with subsequent sulfur atom transfer was also studied, providing thiabicyclo[3.3.0] skeleton in one step with excellent stereocontrol.

Citations

Jan 24, 2008·Chemistry : a European Journal·Laurent ChabaudKurt Schenk
Jul 6, 2013·Chemical Society Reviews·Fabrice DénèsPhilippe Renaud
Jul 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dylan M Lynch, Eoin M Scanlan
Aug 30, 2008·The Journal of Organic Chemistry·Edouard GodineauYannick Landais
Dec 4, 2009·Organic Letters·Tsuyoshi TaniguchiHiroyuki Ishibashi
Dec 29, 2009·Organic Letters·Tsuyoshi Taniguchi, Hiroyuki Ishibashi
Jun 26, 2012·The Journal of Physical Chemistry. a·Chryssostomos ChatgilialogluVitaliy I Timokhin
Jan 5, 2014·Chemical Reviews·Fabrice DénèsPhilippe Renaud
Oct 6, 2006·Organic Letters·Edouard GodineauYannick Landais
Oct 29, 2021·Organic & Biomolecular Chemistry·Qing-Qing KangWen-Ting Wei

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