Journal of Organic Chemistry p. 3906 - 3916 (1994)
Update date:2022-09-26
Topics:
Arjona, Odon
Dios, Alfonso de
Pradilla, Roberto Fernandez de la
Plumet, Joaquin
Viso, Alma
An efficient regio- and stereocontrolled methodology for the alkylative bridge cleavage of oxabicyclic vinyl sulfones is described.A range of 7-oxabicyclo<2.2.1>heptenyl and 8-oxabicyclo<3.2.1>octenyl sulfones has been found to undergo an overall syn SN2' opening when treated with a wide variety of organolithium reagents and lithium aluminum hydride.In this manner, highly functionalized cyclohexenyl and cycloheptenyl sulfones, versatile synthetic intermediates, are now available in high yields.The complete stereoselectivity encountered in the exo conjugate addition may by explained by chelation of the organometallic reagent with the oxygen bridge and steric factors.Furthermore, less-strained substrates allow for complete control of the addition and elimination stages.
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