Abstract

With use of methyl(trifluoromethyl)dioxirane (TFDO), the oxidn. of some tripeptide esters protected at the N-terminus with carbamate or amide groups could be achieved efficiently under mild conditions with no loss of configuration at the chiral centers. Expanding on preliminary investigations, it is found that, while peptides protected with amide groups (PG = Ac, Tfa, Piv) undergo exclusive hydroxylation at the side chain, their analogs bearing a carbamate group [PG = Cbz, Moc, Boc, TcBoc; Moc = COOMe; TcBoc = COOC(Me)2CCl3] give competitive and/or concurrent hydroxylation at the terminal NH moiety. Valuable nitro derivs. are also formed as a result of oxidative deprotection of the carbamate group with excess dioxirane. A rationale is proposed to explain the dependence of the selectivity upon the nature of the protecting group.

Autore Pugliese

• Fusco Caterina

Tutti gli autori

• Annese C.; D'Accolti L.; De Zotti M.; Fusco C.; Toniolo C.; Williard P. G.; Curci R.

Titolo volume/Rivista

Journal of organic chemistry

Anno di pubblicazione

2010

ISSN

0022-3263

ISBN

Non Disponibile

Numero di citazioni Wos

Nessuna citazione

Ultimo Aggiornamento Citazioni

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Numero di citazioni Scopus

Non Disponibile

Ultimo Aggiornamento Citazioni

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Settori ERC

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Codici ASJC

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