Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 2
322
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Aqueous-Phase Synthesis of α-Hydroxyphosphonates Catalyzed by β-Cyclodextrin

, , &
Pages 258-265 | Received 20 Aug 2010, Published online: 14 Sep 2011

REFERENCES

  • Dingwall , J. G. ; Campell , C. D. ; Baylis , E. K. Amino alkane phosphorous acids . U.K. Patent Appl. 1 542 938 1979; Chem. Abstr. 1978 , 88 , 105559j .
  • Engel , R. Phosphonates as analogues of natural phosphonates . Chem. Rev. 1977 , 77 , 349 – 367 .
  • Oiah , G. A. ; Wu , A. Synthetic methods and reactions. 159. Preparation of 1,2-diketones from nonenolizable aliphatic and aromatic acyl chlorides with diethyl 1-alkyl(aryl)-1-(trimethylsiloxy)-methanephosphonates . J. Org. Chem. 1991 , 56 , 902 – 904 .
  • Iorga , B. ; Eymery , F. ; Savignac , P. Controlled monohalogenation of phosphonates: A new route to pure α-monohalogenated diethyl benzylphosphonates . Tetrahedron 1999 , 55 , 2671 – 2686 .
  • Ishiguri , Y. ; Yamada , Y. ; Kato , Y. Y. ; Sasaki , M. ; Mukai , K. Fungicidal composition comprising α-substituted ethylphosphinic acids or their salts, and method of preventing or curing plant diseases using them . Eur. Patent Appl. EP 82–301905, 1982 ; Chem. Abstr. 1983 , 98 , 102686u .
  • Pokalwar , R. U. ; Hangarge , R. V. ; Maske , P. V. ; Shingare , M. S. Synthesis and antibacterial activities of α-hydroxyphosphonates and α-acetyloxyphosphonates derived from 2-chloroquinoline-3-carbaldehyde. Arkivoc. 2006, 11, 196.
  • Patel , D. V. ; Rielly-Gauvin , K. ; Ryono , D. E. Preparation of peptidic α-hydroxy phosphonates a new class of transition state analog renin inhibitors . Tetrahedron Lett. 1990 , 31 , 5587 – 5590 .
  • Gawron , O. ; Grelecki , C. ; Reilly , W. ; Sands , J. Bromomagnesium salts of dialkyl phosphites as intermediates in the synthesis of substituted hydroxymethyl phosphonic acid esters . J. Am. Chem. Soc. 1953 , 75 , 3591 – 3592 .
  • Texier-Boullet , F. ; Lequitte , M. An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride: 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in “dry media.” Tetrahedron Lett. 1986 , 27 , 3515 – 3516 .
  • Smaardijk , A. A. B. ; Noorda , S. ; Bolhuis , F. ; Wynberg , H. The absolute configuration of α-hydroxyphosphonate . Tetrahedron Lett. 1985 , 26 , 493 – 496 .
  • Blazis , V. J. ; Koeller , K. J. ; Spilling , C. D. Reactions of chiral phosphorous acid diamines: The asymmetric synthesis of chiral α-hydroxy phosphonamides, phosphonates, and phosphonic acids . J. Org. Chem. 1995 , 60 , 931 – 940 .
  • Sardarian , A. R. ; Kaboudin , B. Surface-mediated solid phase reactions: Preparation of diethyl 1-hydroxyarylmethylphosphonates on the surface magnesia . Synth. Commun. 1997 , 27 , 543 – 551 .
  • Sonar , S. S. Niobium (V) Chloride catalyzed Abramov reaction: An efficient protocol for the preparation of α-hydroxy phosphonate . Bull. Korean Chem. Soc. 2008 , 29 , 1781 – 1783 .
  • Pamies , O. ; Backvall , J. E. An efficient route to chiral α- and β-hydroxyalkanephosphonates . J. Org. Chem. 2003 , 6 , 4815 – 4818 .
  • Texier-Boullet , F. ; Foucaud , A. Synthesis of 1-hydroxyalkanephosphonic esters on alumina . Synthesis 1982 , 916 .
  • Yokomatsu , T. ; Yamagishi , T. ; Shibuya , S. Enantioselective synthesis of α-hydroxyphosphonates through asymmetric Pudovik reactions with chiral lanthanoid and titaniumalkoxide . J. Chem. Soc. Perkin Trans. 1 1997 , 1527 – 1534 .
  • Azizi , N. ; Saidi , M. R. Lithium perchlorate diethyl ether solution: A highly efficient media for the abramov reaction . Phosphorus, Sulfur, Silicon Relat. Elem. 2003 , 178 , 1255 – 1259 .
  • Heydari , A. ; Arefi , A. ; Khaksar , S. ; Tajbakhsh , M. Hydrophosphonylation of aldehydes catalyzed byguanidine hydrochloride in water . Catal. Commun. 2006 , 7 , 982 – 984 .
  • Murthy , S. N. ; Madhav , B. ; Reddy , V. P. ; Nageswar , Y. V. D. One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water . Tetrahedron Lett. 2010 , 51 , 3649 – 3653 .
  • Zhou , X. ; Liu , X. ; Yang , X. ; Shang , D. ; Xin , J. ; Feng , X. Highly enantioselective hydrophosphonylation of aldehydes catalyzed by tridentate schiff base aluminum(III) complexes. Angew. Chem. Int. Ed. 2008 , 47 , 392 – 394 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.