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, vol.67, no.19, pp.3464-3469, 2011 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 19
  • Publication Date: 2011
  • Doi Number: 10.1016/j.tet.2011.03.036
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.3464-3469
  • Keywords: Acyl phosphonates, Organoaluminum, alpha-Hydroxy phosphonates, PROTEIN-TYROSINE-PHOSPHATASE, ENANTIOSELECTIVE ADDITION, ASYMMETRIC-SYNTHESIS, ANION EQUIVALENTS, HIV PROTEASE, INHIBITORS, ALDEHYDES, ACIDS, ACYLPHOSPHONATES, ANALOGS

Abstract

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.