[2 + 2]-Photocycloaddition of 1,1-Diethoxyethylene to Chiral Polyfunctional 2-Cyclohexenones. Regioselectivity and π-Facial Discrimination

Elena García-Expósito, Ángel Álvarez-Larena, Vicenç Branchadell, Rosa M. Ortuño

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14 Citations (Scopus)

Abstract

The photochemical [2 + 2]-cycloadditions of 1,1-diethoxyethylene to chiral polyfunctional 2-cyclohexenones have been carried out leading to the production of highly constrained unusual α-amino acids with excellent regioselectivity and satisfactory yields. Theoretical calculations have been done to rationalize the observed regio- and diastereoselectivity and show that regiochemistry is determined by the relative rate of formation of the 1,4-biradical intermediates and not by the stability of these species.
Original languageEnglish
Pages (from-to)1120-1125
JournalJournal of Organic Chemistry
Volume69
Issue number4
DOIs
Publication statusPublished - 20 Feb 2004

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