Diastereofacial selectivity in the cycloaddition of nitrones to (E)-γ-oxygenated α,β-unsaturated esters

Félix Busqué, Pedro De March, Marta Figueredo, Josep Font, Montserrat Monsalvatje, Albert Virgili, Ángel Álvarez-Larena, Juan F. Piniella

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35 Citations (Scopus)

Abstract

The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The syn/anti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.
Original languageEnglish
Pages (from-to)8578-8585
JournalJournal of Organic Chemistry
Volume61
Issue number24
Publication statusPublished - 29 Nov 1996

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