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Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2-Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols

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  • This research was supported by the Investigation Program (nos. CTQ2004-06381/BQU, CTQ2004-02367/BQU, and CTQ2007-67492/BQU) of the Ministerio de Educación y Ciencia, Spain and cofinanced by the Fondo Europeo de Desarrollo Regional (FEDER). D.A.-D. and C.R.-F. thank the Ministerio de Ciencia e Innovación, Spain and the I3P-CSIC Program, respectively, for fellowships.

Abstract

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Opened and closed: Visible-light photostimulation of 2,3-diuloses I triggers an unprecedented sequential rearrangement: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization. The contraction of the pyranose ring in this process leads to a new type of cyclopentitol derivative III. R=acyl, alkyl, silyl group.

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