103660-89-5Relevant articles and documents
ASYMMETRIC OXIDATION OF ACHIRAL SELENIDES TO OPTICALLY ACTIVE SELENOXIDES. STEREOCHEMISTRY OF THE ALLYL SELENOXIDE-SELENENATE SIGMATROPIC REARRANGEMENT
Davis, Franklin A.,Stringer, Orum D.,McCauley, John P., Jr.
, p. 4747 - 4758 (1985)
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 sigmatropic rearrangement via an exo transition state is proposed.