Abstract

Pentafluorobenzyl pentafluorophenyl sulfide is oxidised with moderate e.e. value and a low yield by the usually highly successful oxidation protocol based upon tert-butyl hydroperoxide (TBHP) in the presence of a titanium/hydrobenzoin complex. This disappointing result resisted until the present work, in which the switch of the oxidation agent (from TBHP to cumene hydroperoxide), suggested by our previous computations, yielded the enantiopure sulfoxide. This valuable chiral compound was obtained in good yields (76%) without resorting to a chromatographic separation. DFT computations uncovered that this favourable reactivity was originated by a stabilizing π-π-stacking between the phenyl group of the oxidant and the pentafluorophenyl moiety of the substrate.

Autore Pugliese

• Capozzi Maria Annunziata Marcella

Tutti gli autori

• CARDELLICCHIO C.;CAPOZZI M.A.M.

Titolo volume/Rivista

Non Disponibile

Anno di pubblicazione

2018

ISSN

0040-4020

ISBN

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Numero di citazioni Wos

Nessuna citazione

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Numero di citazioni Scopus

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Settori ERC

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Codici ASJC

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