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Synlett 2006(19): 3329-3333
DOI: 10.1055/s-2006-951558
DOI: 10.1055/s-2006-951558
LETTER
© Georg Thieme Verlag Stuttgart · New York
Uncatalyzed Addition of TMSCN to Acylphosphonates
Weitere Informationen
Received
28 August 2006
Publikationsdatum:
23. November 2006 (online)
Publikationsverlauf
Publikationsdatum:
23. November 2006 (online)
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Abstract
The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethylsilyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.
Key words
cyanohydrins - addition reactions - phosphorus - nucleophilic additions
-
1a
Gregory RJH. Chem. Rev. 1999, 99: 3649 -
1b
North M. Tetrahedron: Asymmetry 2003, 14: 147 -
1c
Brunel J.-M.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 -
1d
Kim SS.Kwak JM. Tetrahedron 2006, 62: 49 -
1e
Liu X.Qin B.Zhou X.He B.Feng X. J. Am. Chem. Soc. 2005, 127: 12224 - For reviews on construction of quaternary stereocenters, see:
-
1f
Fuji K. Chem. Rev. 1993, 93: 2037 -
1g
Corey EJ.Guzmanperez A. Angew. Chem. Int. Ed. 1998, 37: 388 -
1h
Christoffers J.Mann A. Angew. Chem. Int. Ed. 2001, 40: 4591 -
2a
Matthews BR.Gountzos H.Jackson WR.Watson KG. Tetrahedron Lett. 1989, 30: 5157 -
2b
Ziegler T.Horsch B.Effenberger F. Synthesis 1990, 575 -
2c
Effenberger F.Stelzer U. Angew. Chem., Int. Ed. Engl. 1991, 30: 873 -
2d
Belokon YN.Green B.Ikonnikov NS.North M.Tararov VI. Tetrahedron Lett. 1999, 40: 8147 -
2e
Belokon YN.Green B.Ikonnikov NS.North M.Parsons T.Tararov VI. Tetrahedron 2001, 57: 771 -
2f
Gröger H. Chem. Rev. 2003, 103: 2795 -
3a
Evans DA.Sarroll GL.Truesdale LK. J. Org. Chem. 1974, 39: 914 -
3b
Evans DA.Truesdale LK. Tetrahedron Lett. 1973, 14: 4929 -
3c
Okino T.Hoashi Y.Takemoto Y. Tetrahedron Lett. 2003, 44: 2817 - 4
North M. Synlett 1993, 807 -
5a For organocatalytical additions of carbon nucleophiles to acyl phosphonates, see:
Reis O. PhD Thesis Middle East Technical University; Ankara: 2005. -
5b
Samanta S.Zhao C.-G. J. Am. Chem. Soc. 2006, 128: 7442 -
6a
Konovalova IV.Burnaeva LA.Saifullina NS.Pudovik AN. Zh. Obshch. Khim. 1976, 46: 18 -
6b
Lebedev EP.Pudovik AN.Tsyganov BN.Nazmutdinov RY.Romanov GV. Zh. Obshch. Khim. 1977, 47: 765 - 7
Kazantsev AV.Averin AD.Lukashev NV.Beletskaya IP. Russ. J. Org. Chem. 1998, 34: 1432 - 8
Demir AS.Reis O.Igdir AC.Esiringu I.Eymur S. J. Org Chem. 2005, 70: 10584 - 9
Shibasaki M.Kanai M.Funabashi K. Chem. Commun. 2002, 1989 - 10
Ryu DH.Corey EJ. J. Am. Chem. Soc. 2004, 126: 8106 ; and references cited therein