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Synthesis 2008(24): 3925-3930  
DOI: 10.1055/s-0028-1083244
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sequential Reaction of Glyoxal Hydrates with α-Bromo Ketones: Synthesis of 2,4,5-Triacyl-1,3-dioxolanes

Qiyun Shao, Wenbo Shi, Chunbao Li*
Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn;
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Publication History

Received 31 July 2008
Publication Date:
01 December 2008 (online)

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Abstract

The sequential reaction between α-bromo ketones and glyoxal hydrates leads to 2,4,5-triacyl-1,3-dioxolanes. The reactions are promoted by a combination of triethylamine and lithium bromide, and a plausible mechanism is proposed. The reaction presumably proceeds via the condensation of glyoxal hydrates, the Williamson reaction and a cyclization sequentially. The reaction conditions are mild and operationally simple. Although the yields of the reactions are moderate, the products are formed stereoselectively.

Key words

glyoxal hydrate - enols - 1,3-dioxolanes - sequential reactions

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Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 686958 (4c). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or email: deposit@ccdc.cam.ac.uk].

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Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 281490 (6b). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or email: deposit@ccdc.cam.ac.uk].