Synthesis of allylic alcohols from oxazolinyloxiranes.
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.
Perna
Filippo M
FM
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.
Capriati
Vito
V
Florio
Saverio
S
Luisi
Renzo
R