Organic Letters p. 2773 - 2776 (2000)
Update date:2022-08-03
Topics:
Adam, Waldemar
Hajra, Saumen
Herderich, Markus
Saha-M?ller, Chantu R.
The catalytic oxidation of the allylic alcohols 1d-n with iodosobenzene diacetate, mediated by the [CrIII(salen)]X complex, affords the respective enones in excellent chemoselectivity for Cl- as counterion [complex A(Cl)], while for the counterions TfO- [complex A(TfO)] and PF6- [complex A(PF6)] nearly equal amounts of enone and epoxide are observed. This counterion-dependent oxidation of allylic alcohols by CrIII(salen) complexes is rationalized in terms of Lewis acid catalysis by the complex A(Cl) and redox catalysis for A(TfO) and A(PF6).
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