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Synthesis of allylic alcohols from oxazolinyloxiranes
Filippo M Perna1, Vito Capriati, Saverio Florio
1C.N.R., Istituto di Chimica dei Composti OrganoMetallici "ICCOM", Sezione di Bari, Dipartimento Farmaco-Chimico, Università di Bari, Via E. Orabona 4, I-70126 Bari, Italy.
The Journal of Organic Chemistry
|November 26, 2002
Abstract:
Lithium diisopropylamide (LDA) (or s-BuLi/TMEDA) in diethyl ether promotes smooth ring opening of oxazolinyl alkyl oxiranes to give oxazolinyl allylic alcohols, which are masked Baylis-Hillman adducts, in good to excellent yields. An E2-E1cb-like syn-beta-elimination is proposed to explain the easy base-promoted isomerization of the studied oxiranes.