Deprotonation of Oxazolinyloxiranes: Formation of Substituted Acyloxiranes

…, V Capriati, S Di Martino, A Abbotto

Index: Florio, Saverio; Capriati, Vito; Di Martino, Serena; Abbotto, Alessandro European Journal of Organic Chemistry, 1999 , # 2 p. 409 - 417

Full Text: HTML

Citation Number: 13

Abstract

Abstract Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at–100 C in Et 2 O furnishes oxazolinyloxiranyllithium compounds [1] 1b, 1i, and 1l 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-tolylepoxyethane (1h) ...