β-Lithiated oxazolinyloxirane 13a, generated by deprotonation of (R*, R*) trisubstituted oxazolinyloxirane 12a with s(-BuLi/TMEDA in Et2O at -100 °C, was found to be chemically and configurationally stable for at least 1 h at this temperature and reacted stereospecifically with electrophiles to give the corresponding tetrasubstituted derivatives 14a-j with complete retention of configuration at the β-carbon.
beta-Lithiation of Oxazolinyloxirane: Synthetic Utility
CAPRIATI, Vito;LUISI, Renzo
2003-01-01
Abstract
β-Lithiated oxazolinyloxirane 13a, generated by deprotonation of (R*, R*) trisubstituted oxazolinyloxirane 12a with s(-BuLi/TMEDA in Et2O at -100 °C, was found to be chemically and configurationally stable for at least 1 h at this temperature and reacted stereospecifically with electrophiles to give the corresponding tetrasubstituted derivatives 14a-j with complete retention of configuration at the β-carbon.File in questo prodotto:
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