86428-22-0Relevant academic research and scientific papers
OXIDATION OF SELENIDES TO SELENOXIDES USING 2-SULFONYLOXAZIRIDINES
Davis, Franklin A.,Stringer, Orum D.,Billmers, Joanne M.
, p. 1213 - 1216 (1983)
Application of 2-sulfonyloxaziridine, 9, for the "one-pot" transformation of selenides to alkenes and the rearrangement of allylic selenides to allylic alcohols are described.
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 (2007/10/02)
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.
