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


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Seven O., Polat-Cakir S., Hossain M. S. , Emrullahoglu M., DEMİR A. G.

TETRAHEDRON, cilt.67, ss.3464-3469, 2011 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 67 Konu: 19
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.tet.2011.03.036
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.3464-3469

Özet

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.