Journal of Organic Chemistry p. 809 - 815 (1991)
Update date:2022-07-30
Topics:
Davis, Franklin A.
ThimmaReddy, R.
McCauley, John P.
Przeslawski, Robert M.
Harakal, Mark E.
Carroll, Patrick J.
The synthesis and asymmetric oxidations of chiral nonracemic 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides (6) are described.These new N-sulfonyloxaziridines are prepared by oxidation of the corresponding enantiomerically pure sulfonimines 5.These reagents oxidize sulfides to sulfoxides (11-52percent ee), epoxidize nonfunctionalized alkenes (17-61percent ee), and oxidize enolates to α-hydroxy carbonyl compounds (11-81percent ee).Epoxidation of (-)-(S)-limonene with (+)-(2R,3S)-6a, a double asymmetric synthesis, affords a 93:7 cis/trans mixture of limonene oxides.Evaluation ofpossible transition-state structures suggests that the molecular recognition is primarily determined by steric factors.These reagents are less effective than N-sulfonyloxaziridines 1-3 in their asymmetric oxidations because they lack well-defined regions that are topologically dissimilar near the active site.
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