Deprotonation of oxazolinyl oxirane 1a with sec-BuLi/TMEDA at -100 °C in Et20 furnished oxazolinyl oxiranyllithium 1b, which could be trapped with electrophiles to give oxiranes 1c-g. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-oxazolinyl-2-p-tolyl epoxy ethane 1h was found to be configurationally stable while oxiranyllithium 1I, generated from the cis isomer 1k, was not. Oxazolinyl epoxides 1d, 1j and 1m could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e.
An Efficient Synthesis of Oxiranyl oxazolines and Elaboration to Acyl Oxiranes
CAPRIATI, Vito;
1998-01-01
Abstract
Deprotonation of oxazolinyl oxirane 1a with sec-BuLi/TMEDA at -100 °C in Et20 furnished oxazolinyl oxiranyllithium 1b, which could be trapped with electrophiles to give oxiranes 1c-g. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-oxazolinyl-2-p-tolyl epoxy ethane 1h was found to be configurationally stable while oxiranyllithium 1I, generated from the cis isomer 1k, was not. Oxazolinyl epoxides 1d, 1j and 1m could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
