Straightforward Synthesis of 1,2-Amino Phosphate Diesters and Application to the Synthesis of Novel 1,2-Amino Ether Diesters

REFERENCES

• Hwu , J. R. ; Hakimelahi , G. H. ; Sambaiah , T. ; Patel , H. V. ; Tsay , S. C. ; Lai , Y. K. ; Lieu , C. H. Design and synthesis of new taxol-containing aminophosphates as protaxols . Bioorg. Med. Chem. Lett. 1997 , 7 , 545 – 548 .
   Web of Science ®Google Scholar
• (a) Goujon , J. Y. ; Gueyrard , D. ; Compain , P. ; Martin , O. R. ; Asano , N. Ring-opening reaction of iminosugar-derived aziridines: Application to the general synthesis of α-1-C-substituted derivatives of fagomine . Tetrahedron: Asymmetry 2003 , 14 , 1969 – 1972 ; (b) Goujon , J. Y. ; Gueyrard , D. ; Compain , P. ; Martin , O. R. ; Ikeda , K. ; Kato , A. ; Asano , N. General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides) . Bioorg. Med. Chem. 2005 , 13 , 2313 – 2324 .
   Web of Science ®Google Scholar
• (a) Uchiyama , M. ; Aso , Y. ; Noyori , R. ; Hayakawa , Y. O-Selective phosphorylation of nucleosides without N-protection . J. Org. Chem. 1993 , 58 , 373 – 379 ; (b) Hayakawa , Y. ; Kawai , R. ; Kataoka , M. Nucleotide synthesis via methods without nucleoside-base protection . Eur. J. Pharm. Sci. 2001 , 13 , 5 – 16 .
   Web of Science ®Google Scholar
• Cardenas , G. ; Cabrera , G. ; Taboada , E. ; Rinaudo , M. Synthesis and characterization of chitosan alkyl phosphate . J. Chil. Chem. Soc. 2006 , 51 , 815 – 820 .
   Web of Science ®Google Scholar
• (a) Prasad , B. A. B. ; Sanghi , R. ; Singh , V. K. Studies on ring cleavage of aziridines with hydroxyl compounds . Tetrahedron 2002 , 58 , 7355 – 7363 , and references cited therein; (b) Yadav , J. S. ; Reddy , B. V. S. ; Balanarsaiah , E. ; Raghavendra , S. Montmorillonite clay–catalyzed cleavage of aziridines with alcohols . Tetrahedron Lett. 2002 , 43 , 5105 – 5107 ; (c) Hodgson , D. M. ; Stefane , B. ; Miles , T. J. ; Witherington , J. Organolithium-induced alkylative ring opening of aziridines: Synthesis of unsaturated amino alcohols and ethers . J. Org. Chem. 2006 , 71 , 8510 – 8515 .
   Web of Science ®Google Scholar
• (a) Ho , M. ; Chung , J. K. K. ; Tang , N. A convenient synthesis of chiral N-boc-amino ethers as potential peptide bond surrogate units . Tetrahedron Lett. 1993 , 34 , 6513 – 6516 ; (b) Harrison , T. ; Willams , B. J. ; Swain , C. Gem-disubstituted amino-ether–based substance P antagonists . J. Bioorg. Med. Chem. Lett. 1994 , 4 , 2733 – 2734 .
   Web of Science ®Google Scholar
• (a) LaMontagne , M. P. ; Ao , M. S. ; Markovac , A. ; Menke , J. R. Antimalarials, 8: Synthesis of amino ethers as candidate antimalarials . J. Med. Chem. 1975 , 19 , 360 – 365 ; (b) Boger , D. L. ; Kim , S. H. ; Mori , Y. ; Weng , J. H. ; Rogel , O. ; Castle , S. L. ; Mc Atee , J. J. First and second generation total synthesis of the teicoplanin aglycon . J. Am. Chem. Soc. 2001 , 123 , 1862 – 1871 .
   Web of Science ®Google Scholar
• Dwivedi , S. K. ; Gandhi , S. ; Rastogi , N. ; Singh , V. K. Lewis acid–catalyzed regioselective ring opening of azetidines with alcohols and thiols. Tetrahedron Lett. 2007, 48, 5375–5377, and references cited therein.
   Web of Science ®Google Scholar
• (a) Ramirez , A. ; Lobkovsky , E. ; Collum , D. B. Hemilabile ligands in organolithium chemistry: Substituent effects on lithium ion chelation . J. Am. Chem. Soc. 2003 , 125 , 15376 – 15387 ; (b) Okuda , M. ; Tomioka , K. Stereo- and regiochemical aspects of the Mitsunobu reaction in synthesis of chiral amino ether ligands for asymmetric reactions . Tetrahedron Lett. 1994 , 35 , 4585 – 4586 .
   PubMed Web of Science ®Google Scholar
• Besbes , R. ; Ennigrou , M. R. A simple and direct synthesis of erythro-β-amino-α-hydroxy esters from trans-β-phenylglycidic ester . Synth. Commun. 2004 , 34 , 2185 – 2194 .
   Web of Science ®Google Scholar
• Ould Elemine , B. ; Besbes , R. ; Ennigrou , M. R. Pratical preparation of β-amino-α-hydroxy diesters: Key intermediates for 1,4-oxazin-2-ones . Synth. Commun. 2007 , 37 , 3989 – 4004 .
   Web of Science ®Google Scholar
• (a) Sauvé , G. ; Le Berre , N. ; Zacharie , B. Novel modifications of peptides: Simple syntheses of difunctionalized enamines, enol ethers, and thioenol ethers from carboxylic acids via acylimidazole and enol phosphate intermediates . J. Org. Chem. 1990 , 55 , 3002 – 3004 ; (b) Dorn , V. B. Diethyl chlorophosphate . Synlett 2005 , 20 , 3171 – 3172 .
   Web of Science ®Google Scholar
• Bhanu Prasad , B. A. ; Sanghi , R. ; Singh , V. K. Studies on ring cleavage of aziridines with hydroxyl compounds . Tetrahedron 2002 , 58 , 7355 – 7363 .
   Google Scholar