Synthesis of allylic alcohols from oxazolinyloxiranes |
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| Authors: | Perna Filippo M Capriati Vito Florio Saverio Luisi Renzo |
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| Affiliation: | C.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. |
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| 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. |
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