Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates

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Date

2011-05-13

Author

Seven, Ozlem
Polat-Cakir, Sidika
Hossain, Md. Shakhawoat
Emrullahoglu, Mustafa
Demir, Ayhan Sıtkı

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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.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/62983

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2011.03.036

Collections

Department of Chemistry, Article

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Citation Formats

O. Seven, S. Polat-Cakir, M. S. Hossain, M. Emrullahoglu, and A. S. Demir, “Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates,” TETRAHEDRON, pp. 3464–3469, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62983.