Journal of Organic Chemistry p. 5123 - 5128 (1998)
Update date:2022-07-29
Topics:
Kouklovsky, Cyrille
Dirat, Olivier
Berranger, Thierry
Langlois, Yves
Tran-Huu-Dau, Marie Elise
Riche, Claude
Oxazoline N-oxide 2 in the presence of α,β-unsaturated esters or nitroalkenes afforded the corresponding adducts with excellent regio- and stereoselectivities depending of the substitution pattern on the dipolarophile. Especially, inversion of regioselectivity was observed by switching from a 1,2-disubstituted to a 1,1-disubstituted α,β-unsaturated ester. This was not observed when nitroalkenes are used as dipolarophiles. An attempt to rationalize the observed selectivities by semiempirical calculations at RHF AM1 level is described. The cycloadduct 5e has been used as the starting material in a total synthesis of the pheromone (-)-frontalin 12.
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