Diphenyl methylphosphonate as a phosphonylation reagent with high diastereoselectivity at phosphorus

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2597-2600

  Moriarty, Robert M ^a   Tao, Anping ^a   Condeiu, Cristian ^a   Gilardi, Richard ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030958215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00423-1     Document Type: Article

References (20)

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14. Bis(4-nitrophenyl) methylphosphonate was reported to be a good reagent for phosphonation via transesterification in the presence of DBU (Tawfik, D. S.; Eshhar, Z.; Bentolila, A.; Green, B. S. Synthesis 1993, 968). However, the use of DBU can lead to P-epimerization, thus lowering the diastereoselectivity at the phosphorus chiral center (Lesnikowski, Z. J.; Zabawska, D.; Jaworska,-Maslanka, M. M.; Schinazi, R. F.; Stec, W. J. New J. Chem. 1994, 18, 1197).
15. Bis(4-nitrophenyl) methylphosphonate was reported to be a good reagent for phosphonation via transesterification in the presence of DBU (Tawfik, D. S.; Eshhar, Z.; Bentolila, A.; Green, B. S. Synthesis 1993, 968). However, the use of DBU can lead to P-epimerization, thus lowering the diastereoselectivity at the phosphorus chiral center (Lesnikowski, Z. J.; Zabawska, D.; Jaworska,-Maslanka, M. M.; Schinazi, R. F.; Stec, W. J. New J. Chem. 1994, 18, 1197).
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