Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at - 100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds 1b, 1i, and 1I which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxy-ethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.
Deprotonation of Oxazolinyloxiranes: Formation of Substituted Acyloxiranes
CAPRIATI, Vito;
1999-01-01
Abstract
Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at - 100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds 1b, 1i, and 1I which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxy-ethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
