Oxaziridinium salts -norephedrine derivative

As shown in cycle (b) in Scheme 10.1, the iminium-oxaziridinium pair can also effect catalytic asymmetric epoxidation of alkenes. Early work in this field by Bohe et al. included investigation of the norephedrine-derived oxaziridinium salt 34 (33% ee in the catalytic epoxidation of traws-stilbene [41] ee up to 61% was achieved when 34 was employed stoichiometrically [42]), or the L-proline-derived material 35 (39% ee in the epoxidation of trans-3-phenyl-2-propenol [43]). Rapid... 

Using an oxaziridinium salt derived from dihydroisoquinoline, Lusinchi was able to transfer the oxygen atom to several simple alkenes in good yield (Scheme 5.2) [5,6]. Following this work, the first enantiomerically pure oxaziridinium salt was prepared [7]. Quaternization of chiral oxaziridine (1), derived from (lS,2R)-(+)-norephedrine, produced the oxaziridinium salt (2) (Scheme 5.3). 

Scheme 1.26 The first enantiomericaUy pure oxaziridinium salt derived from (lS,2R)-(+)-norephedrine...

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See also in sourсe #XX -- [ ]

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