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.

Synthesis of Allylic Alcohols from Oxazolinyloxiranes

PERNA, FILIPPO;CAPRIATI, Vito;LUISI, Renzo
2002-01-01

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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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/121236
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