The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent
Heteroatom-assisted isomerization of oxiranes to allylic alcohols promoted by bases
Mordini Alessandro;Reginato Gianna;
1994
Abstract
The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituentFile in questo prodotto:
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