Abstract

With use ofmethyl(trifluoromethyl)dioxirane (TFDO), the oxidation 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 analogues bearing a carbamate group (PG=Cbz-, Moc-, Boc-, TcBoc-) give competitive and/or concurrent hydroxylation at the terminalN-Hmoiety. Valuable nitro derivatives 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

• D'accolti Lucia

Tutti gli autori

• D'ACCOLTI L.

Titolo volume/Rivista

Non Disponibile

Anno di pubblicazione

2010

ISSN

0022-3263

ISBN

Non Disponibile

Numero di citazioni Wos

16

Ultimo Aggiornamento Citazioni

Non Disponibile

Numero di citazioni Scopus

46

Ultimo Aggiornamento Citazioni

Non Disponibile

Settori ERC

Non Disponibile

Codici ASJC

Non Disponibile