Tetrahedron p. 4747 - 4758 (1985)
Update date:2022-08-04
Topics: Stereochemistry Optically active Asymmetric Oxidation Allyl Achiral Selenides Selenoxides Sigmatropic rearrangement
Davis, Franklin A.
Stringer, Orum D.
McCauley, John P., Jr.
Asymmetric oxidation of methyl phenyl selenide (3), under anhydrous conditions, by chiral 2-sulfonyloxaziridines, 1-2, give optically active methyl phenyl selenoxide (8.1-9.3percent ee).The stereochemistry of the selenoxide is determined by the configuration of the oxaziridine three membered ring with nonbonded steric interactions responsible for the chiral recognition.Asymmetric oxidation of E-phenyl cinnamyl selenide (7) by 1-2 affords optically active 1-phenylallyl alcohol (9).A concerted <2,3> sigmatropic rearrangement via an exo transition state is proposed.
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Doi:10.1016/S0040-4020(01)96683-9
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