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Synfacts 2009(1): 0050-0050  
DOI: 10.1055/s-0028-1087403
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Sequential Photoelimination and Aldol Cyclization of 1,2-Diketones

Contributor(s): Mark Lautens, Jane Panteleev
D. Álvarez-Dorta, E. I. León*, A. R. Kennedy, C. Riesco-Fagundo, E. Suárez*
Instituto de Productos Naturales y Agrobiologio del CSIC, Tenerife, Spain and WestCHEM, University of Strathclyde, Glasgow, UK
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

The authors report a unique photochemical rearrangement of non-2,3-diuloses 1. Upon irradiation with a daylight lamp, a Norrish type II photoelimination occurs followed by an ­aldol cyclization, forming the corresponding ­bicyclic products 2, in moderate yield. High dia­stereoselectivity is achieved, with epimers observed only at the hemiacetal.