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Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols

Alvarez-Dorta, D. and Leon, E.I. and Kennedy, A.R. and Riesco-Fagundo, C. and Suarez, E. (2008) Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols. Agewandte Chemie-International Edition, 47 (46). pp. 8917-8919. ISSN 1433-7851

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Abstract

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.