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DOI: 10.1055/s-2006-926349
Synthesis of Novel Enantiomerically Pure C 3-Symmetric Trialkanolamine Ligand Containing Phosphoryl Groups
Publication History
Publication Date:
27 February 2006 (online)
Abstract
Catalytic activity of ten metal salts in the reaction of benzhydrylamine and benzylamine with diethyl 2,3-epoxypropylphosphonate (1) was studied. Only in the presence of copper(I) iodide pure diethyl 3-benzhydrylamino- and 3-benzylamino-2-hydroxypropylphosphonates were produced quantitatively. Although the reactions catalysed by calcium(II) triflate were the fastest, they led to the contamination of the major products with the respective bisphosphonates. Enantiomerically pure (S,S)-bis[2-(O,O-diethylphosphorylmethyl)ethanol]amine (10) was prepared in a Ca(OTf)2-catalysed reaction of (S)-1 (ee 94%) with 0.4 equivalent benzylamine followed by hydrogenolysis. The bisphosphonate (S,S)-10 was transformed into enantiomerically pure (S,S,S)-tris[2-(O,O-diethylphosphorylmethyl)ethanol]amine (2), when reacted with (S)-1 (ee 94%) or into (R,S,S)-2, when (R)-1 (ee 94%) was used.
Key words
amino alcohols - epoxides - ligands - phosphonates - ring opening
- 1
Grassi M.Di Silvestro G.Farina M. Tetrahedron 1985, 41: 177 - 2
Nugent WR.Harlow RL. J. Am. Chem. Soc. 1994, 116: 6142 - 3
Moberg C. Angew. Chem. Int. Ed. 1998, 37: 248 - 4
Di Furia F.Licini G.Modena G.Motterle R.Nugent WA. J. Org. Chem. 1996, 61: 5175 - 5
Bonchio M.Licini G.Di Furia F.Mantovani S.Modena G.Nugent WA. J. Org. Chem. 1999, 64: 1326 - 6
Nugent WA. J. Am. Chem. Soc. 1992, 114: 2768 - 7
Nugent WA. J. Am. Chem. Soc. 1998, 120: 7139 - 8
Buonomenna MG.Drioli E.Nugent WA.Prins LJ.Scrimin P.Licini G. Tetrahedron Lett. 2004, 45: 7515 - 9
Gao Y.Hanson RM.Klunder JM.Ko SY.Masamune H.Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765 - 10
Miyano S.Lu LD.-L.Viti SM.Sharpless KB. J. Org. Chem. 1983, 48: 3608 - 11
Michaelson RC.Palermo RE.Sharpless KB. J. Am. Chem. Soc. 1977, 99: 1990 - 12
Bolm C.Bienewald F. Angew. Chem., Int. Ed. Engl. 1995, 34: 2640 - 13
Mase N.Ohno T.Hoshikawa N.Ohishi K.Morimoto H.Yoda H.Takabe K. Tetrahedron Lett. 2003, 44: 4073 - 14
Black CA.Ucci JW.Vorpagel JS.Mauck MC.Fenlon EE. Bioorg. Med. Chem. Lett. 2002, 12: 3521 - 15
Dro C.Bellemin-Laponnaz S.Welter R.Gade LH. Angew. Chem. Int. Ed. 2004, 43: 4479 - 16
Kim S.-G.Kim K.-H.Kim YK.Shin SK.Ahn KH. J. Am. Chem. Soc. 2003, 125: 13819 - 17
Castaldi MP.Gibson SE.Rudd M.White AJP. Angew. Chem. Int. Ed. 2005, 44: 3432 - 18
Bringmann G.Pfeifer R.-M.Rummey C.Hartner K.Breuning M. J. Org. Chem. 2003, 68: 6859 - 19
Gautier A.Mulatier J.-C.Crassous J.Dutasta J.-P. Org. Lett. 2005, 7: 1207 - 20
Kiss T.Lazar I. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological ActivityKukhar VP.Hudson HR. Wiley; New York: 2000. p.285-326 - 21
Wróblewski AE.Haajewska-Wosik A. Eur. J. Org. Chem. 2002, 2758 - 22
Wróblewski AE.Haajewska-Wosik A. Tetrahedron: Asymmetry 2003, 14: 3359 - 23
Wróblewski AE.Haajewska-Wosik A. Tetrahedron: Asymmetry 2004, 15: 3201 - 24
Jacobsen EN. Acc. Chem. Res. 2000, 33: 421 - 25
Favretto L.Nugent WA.Licini G. Tetrahedron Lett. 2002, 43: 2581 - 26
Righi G.Pescatore G.Bonadies F.Bonini C. Tetrahedron 2001, 57: 5649 - 27
Zhao P.-Q.Xu L.-W.Xia C.-G. Synlett 2004, 846 - 28
Chakraborti AK.Rudrawar S.Kondaskar A. Eur. J. Org. Chem. 2004, 3597 - 29
Cepanec I.Litvi M.Mikuldaš H.Bartolinčić A.Vinković V. Tetrahedron 2003, 59: 2435