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An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes

โœ Scribed by Saverio Florio; Vito Capriati; Serena Di Martino

Book ID
104259568
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
259 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Deprotonation of oxazolinyl oxirane la with sec-BuLi/TMEDA at -100 ยฐC in Et20 furnished oxazolinyl oxiranyllithium lb, which could be trapped with electrophiles to give oxiranes lc-g. The reaction of lb with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium li from trans-l-oxazolinyl-2p-tolyl epoxy ethane lh was found to be configurationally stable while oxiranyllithium 11, generated from the cis isomer lk, was not. Oxazolinyl epoxides ld, lj and lm could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e.

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