ISSN:
1434-193X
Keywords:
Deprotonation
;
Oxiranyloxazolines
;
Oxazolinyloxiranyllithium compounds
;
Oxazolidines
;
Acyloxiranes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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