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Deprotonation of Oxazolinyloxiranes: Formation of Substituted Acyloxiranes (1999)

Florio, Saverio ; Capriati, Vito ; Di Martino, Serena ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 409-417

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Details

ISSN: 1434-193X

Schlagwort(e): Deprotonation ; Oxiranyloxazolines ; Oxazolinyloxiranyllithium compounds ; Oxazolidines ; Acyloxiranes ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at -100 °C in Et2O 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) 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.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

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