Synthesis of allylic alcohols from oxazolinyloxiranes.

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.