Journal
TETRAHEDRON
Volume 67, Issue 19, Pages 3464-3469Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.036
Keywords
Acyl phosphonates; Organoaluminum; alpha-Hydroxy phosphonates
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Funding
- Scientific and Technological Research Council of Turkey (TUBITAK)
- Turkish Academy of Science (TUBA)
- Middle East Technical University (METU)
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The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they afford the tertiary alpha-hydroxy phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.
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