Abstract
Aldehydes were found to undergo facile stereoselective vinyloxiranation with the lithium dienolate of ethyl 2-bromocrotonate ( 12) at low temperature. The resulting vinyloxiranes were transformed thermolytically to functionalized dihydrofurans. An operational comparison of this heterocyclic annulation is made with its carbocyclic counterpart, the [2+3] cyclopentene annulation, and the potential for a general dihydrofuran synthesis in either a racemic or an asymmetric fashion is addressed.
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