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Synfacts 2010(3): 0319-0319  
DOI: 10.1055/s-0029-1219333
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Radical Cyclization of α-Bromo Aluminum Acetals

Contributor(s): Mark Lautens, Jane Panteleev
A. Boussonnière, F. Dénès*, J. Lebreton*
Université de Nantes, France
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Publikationsdatum:
18. Februar 2010 (online)

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Significance

The radical cyclization of α-halo­acetals onto double bonds (Ueno-Stork reaction) can be a useful method for the synthesis of cyclic acetals (see Review below). The synthesis of the acetal starting materials can be challenging and incompatible with acid-sensitive functional groups. The authors utilize α-bromoesters directly in this transformation by forming aluminum acetals in situ through reduction of esters with DIBAL-H, which then undergo radical cyclization.

Review: X. J. Salom-Roig, F. Dénès, P. Renaud Synthesis 2004, 1903-1928.