Acetals of γ-oxo-α,β-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications

Ramon Alibés, Félix Busquè, Pedro De March, Marta Figueredo, Josep Font, Maria Esmeralda Gambino, Brian A. Keay

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10 Citations (Scopus)

Abstract

Several acetals of γ-oxo-α,β-unsaturated esters have been prepared, mainly from enantiopure C2-symmetric diols, and their 1,3-dipolar cycloaddition to 2,3,4,5-tetrahydropyridine 1-oxide has been studied. All the reactions showed complete regioselectivity and a high preference for the endo approach of the reactants in the transition state. The enantiopure acetals derived from (cis,cis)-spiro[4.4]nonane-1,6-diol gave the highest diastereofacial selectivity. © 2001 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1747-1756
JournalTetrahedron Asymmetry
Volume12
Issue number12
DOIs
Publication statusPublished - 16 Jul 2001

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