This work was supported by the French Ministry of Science. We would like to thank Nathali Henriques, Christian Duchamp, and Dr. Denis Bouchu (Centre Commun de Spectroscopie de Masse—Université Claude Bernard Lyon 1—France) for HRMS measurements.
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Communication
Radical Cyclization of α-Bromo Aluminum Acetals: An Easy Approach to γ-Lactols†
Article first published online: 10 NOV 2009
DOI: 10.1002/anie.200905167
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Boussonnière, A., Dénès, F. and Lebreton, J. (2009), Radical Cyclization of α-Bromo Aluminum Acetals: An Easy Approach to γ-Lactols. Angew. Chem. Int. Ed., 48: 9549–9552. doi: 10.1002/anie.200905167
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Publication History
- Issue published online: 30 NOV 2009
- Article first published online: 10 NOV 2009
- Manuscript Received: 15 SEP 2009
Funded by
- French Ministry of Science
Keywords:
- aluminum acetals;
- cyclization;
- γ-lactols;
- radical reactions
Running rings around aluminum: An efficient procedure for radical cyclization of α-bromo esters is reported. Reduction of the esters by DIBAL-H at low temperature gives aluminum acetals, which are cyclized in the presence of nBu3SnH and Et3B (see scheme). These one-pot conditions lead to polysubstituted γ-lactols in high yields, and the mildness of the reaction conditions allows the preparation of acid-sensitive derivatives.