Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(21): 3447-3452
DOI: 10.1055/s-0028-1083176
DOI: 10.1055/s-0028-1083176
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkEfficient Diastereoselective Synthesis of Phosphonato Vinylsulfones via a Multicomponent Method
Further Information
Received
9 May 2008
Publication Date:
16 October 2008 (online)
Publication History
Publication Date:
16 October 2008 (online)

Abstract
The phosphonato vinylsulfone building block was prepared by a facile three-component reaction of an acetylene, a sulfonyl chloride and a trialkyl phosphite.
Key words
vinylsulfone - dialky acetylenedicarboxylate - trialkyl phosphate - multicomponent reaction - zwitterion
- 1a
Simpkins NS. Sulfones in Organic Synthesis Pergamon; Oxford: 1993. - 1b
Tanaka K.Kaji A. In The Chemistry of Sulfones and SulfoxidesPatai S.Rapoport Z.Stirling CJM. Wiley; Chechester: 1988. Chap. 15. - 1c
Carreno MC. Chem. Rev. 1995, 95: 1717 - 1d
Kazuhiro Y.Tamio H. J. Am. Chem. Soc. 2003, 125: 2872 - 1e
Ranu BC.Guchhait SK.Ghosh K. J. Org. Chem. 1998, 63: 5250 - 1f
Fuchs PL.Braish TF. Chem. Rev. 1986, 86: 903 - 1g
De Lucchi O.Pasquato L. Tetrahedron 1988, 44: 6755 - 1h
Wang G.Mahesh U.Chen GYJ.Yao SQ. Org. Lett. 2003, 5: 737 - 1i
Katritzky AR.Huang T.-B.Voronkov MV.Wang M.Kolb H. J. Org. Chem. 2000, 65: 8819 - 1j
Freihammer PM.Detty MR. J. Org. Chem. 2000, 65: 7203 - 1k
Reddy PE, andReddy RMV. inventors; PCT Int. Appl. W09918068. ; Chem. Abstr. 1999, 130, 281870 - 1l
Konopa JK,Konieczny MT,Horowska BJ,Kunikowski AJ,Asao T,Nishino H, andYamada Y. inventors; Jpn. Patent JP 9003037. ; Chem. Abstr. 1997, 126, 185889 - 2 For a review of desulfonylation,
see:
Najera C.Yus M. Tetrahedron 1999, 55: 10547 - 3a
Kaboudin B.Nazari R. Tetrahedron Lett. 2001, 42: 8211 - 3b
Kim DY.Rhie DY. Tetrahedron 1997, 53: 13603 ; and references therein - 3c
Thomas AA.Sharpless KB. J. Org. Chem. 1999, 64: 8379 - 3d
Shen Y.Jiang GF. Synthesis 2000, 99 - 3e
Tago K.Kogen H. Org. Lett. 2000, 2: 1975 - 4a
Huang X.Duan D.Zheng W. J. Org. Chem. 2003, 68: 1958 - 4b
Duan D.-H.Huang X. Synlett 1999, 317 - 4c
Huang X.Liang C.-G.Xu Q.He Q.-W. J. Org. Chem. 2001, 66: 74 - 4d
Nair V.Augustine A.George TG.Nair LG. Tetrahedron Lett. 2001, 42: 6763 - 4e
Qian H.Huang X. Synlett 2001, 1913 - 4f
Berteina S.Wendeborn S.Brill WK.-D.Mesmaeker AD. Synlett 1998, 676 - 4g
Matano Y.Yoshimune M.Azuma N.Suzuki H. J. Chem. Soc., Perkin Trans. 1 1996, 1971 - 5
Tietze LF. Chem. Rev. 1996, 96: 115 - 6
Ugi I. Angew. Chem., Int. Ed. Engl. 1982, 21: 810 - 7
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3169 - 8
Dömling A. Chem. Rev. 2006, 106: 17 - 9a
Alizadeh A.Masrouri H.Rostamnia S.Movahedi F. Helv. Chim. Acta. 2006, 89: 923 - 9b
Alizadeh A.Rostamnia S.Hu ML. Synlett 2006, 1592 - 9c
Alizadeh A.Rostamnia S.Esmaili AA. Synthesis 2007, 709 - 9d
Alizadeh A.Oskueyan Q.Rostamnia S. Synthesis 2007, 2637 - 9e
Alizadeh A.Zohreh N.Rostamnia S. Tetrahedron 2007, 63: 8083 - 9f
Alizadeh A.Rostamnia S. Synthesis 2008, 57 - 9g
Alizadeh A.Rostamnia S.Zohreh N.Bijanzadeh HR. Monatsh. Chem. 2008, 139: 49 - 9h
Alizadeh A.Rostamnia S.Zhu LG. Tetrahedron 2006, 62: 5641 - 9i
Alizadeh A.Rostamnia S.Zohreh N.Oskueyan Q. Synlett. 2007, 1610 - 10a
Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis: Organic Compounds and Metal Complexes
Vol. 8:
Verkade JG.Quin LD. VCH; New York: 1987. p.401 - 10b
Duncan M.Gallagher MJ. Org. Magn. Reson. 1981, 15: 37 - 10c
Ahlbrecht H.Farnung W. Chem. Ber. 1984, 117: 1 - 10d
Macomber RS.Krudy GA. J. Org. Chem. 1981, 46: 4038 - 11a
Johnson AW.Tebby JC. J. Chem. Soc. 1961, 2126 - 11b
Tebby JC.Wilson IF.Griffiths DV. J. Chem. Soc., Perkin Trans. 1 1979, 2133 - 11c
Winterfeldt E.Dillinger H.-J. Chem. Ber. 1966, 99: 1558 - 11d
Nozaki K.Sato N.Ikeda K.Takaya H. J. Org. Chem. 1996, 61: 4516 - 11e
Nair V.Nair JS.Vinod AU.Rath NP. J. Chem. Soc., Perkin Trans. 1 1997, 3129 - 11f
Nair V.Nair JS.Vinod AU. Synthesis 2000, 1713 - 11g
Yavari I.Alizadeh A.Mohebbi H. Phosphorus, Sulfur 2003, 178: 1741 - 11h
Yavari I.Maghsoodlou MT. Tetrahedron Lett. 1998, 39: 4579