Tetrahedron

Cyclopropanespiro-β-lactones derived from 4-[(Z)-ethylidene]-3-methyloxetan-2-one: diastereoselective formation and rearrangement reactions

NWA Geraghty, P McArdle, LMA Mullen

Index: Geraghty, Niall W.A.; McArdle, Patrick; Mullen, Laverne M.A. Tetrahedron, 2011 , vol. 67, # 19 p. 3546 - 3552

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Citation Number: 3

Abstract

Abstract The metal catalysed reaction of monosubstituted diazo esters and ketones with 4- [(Z)-ethylidene]-3-methyloxetan-2-one results in the formation of cyclopropanespiro-β- lactones. In contrast to most alkene cyclopropanations, including those involving diketene, the reaction occurs diastereoselectively. A computational model of the reaction has been developed that accounts for the observed stereochemistry. The metal promoted thermal ...