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 2003(3): 0343-0345
DOI: 10.1055/s-2003-37352
DOI: 10.1055/s-2003-37352
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
An Easy Access to (E)-Alkylidenesuccinic Acids [1]
Further Information
Received
15 October 2002
Publication Date:
19 February 2003 (online)
Publication History
Publication Date:
19 February 2003 (online)
Abstract
A two-step simple, efficient and general approach to (E)-alkylidenesuccinic acids 1a-e has been demonstrated in 82-88% overall yields via condensation of Wittig adduct of maleimide 2 and triphenylphosphine with aliphatic aldehydes followed by acid-catalyzed hydrolysis pathway.
Key words
maleimide-triphenylphosphine adduct - aliphatic aldehydes - condensations - hydrolysis - alkylidenesuccinic acids
NCL Communication No. 6632.
- 2
Devlin JP.Ollis WD.Thorpe JE.Wood RS.Broughton BJ.Warren PJ.Wooldbridge KRH.Wright DE. J. Chem. Soc., Perkin Trans. 1 1975, 830 - 3
Broughton BJ.Warren PJ.Wooldbridge KRH.Wright DE.Ollis WD.Wood RJ. J. Chem. Soc., Perkin Trans. 1 1975, 842 - 4
Porter NA.Scott DM.Rosenstein IJ.Giese B.Veit A.Zeitz HG. J. Am. Chem. Soc. 1991, 113: 1791 - 5
Levy DE.Lapierre F.Liang W.Ye W.Lange CW.Li X.Grobelny D.Casabonne M.Tyrrell D.Holme K.Nadzan A.Galardy RE. J. Med. Chem. 1998, 41: 199 - 6
Groutas WC.Brubaker MJ.Stanga MA.Castrisos JC.Crowley JP.Schatz EJ. J. Med. Chem. 1989, 32: 1607 - 7
Bates RB.Cuther RS.Freeman RM. J. Org. Chem. 1977, 42: 4162 -
8a
Kofron WG.Wideman LG. J. Org. Chem. 1972, 37: 555 -
8b
Sabitha G.Srividya R.Yadav JS. Tetrahedron 1999, 55: 4015 -
8c
Chen Y.Deng L. J. Am. Chem. Soc. 2001, 123: 11302 -
8d
Bergmeier SC.Ismail KA. Synthesis 2000, 1369 - 9
Giese B.Kretzchmar G.Meixner J. Chem. Ber. 1980, 113: 2787 - 10
Cermenati L.Mella M.Albini A. Tetrahedron 1998, 54: 2575 - 11
Horning EC.Walker GN. J. Am. Chem. Soc. 1952, 74: 5147 - 12
Doulut S.Dubuc I.Rodriguez M.Vecchini F.Fulcrand H.Bareli H.Checler F.Bourdel E.Aumelas A.Lallement JC.Kitabgi P.Costentin J.Martinez J. J. Med. Chem. 1993, 36: 1369 - 13
Nogi T.Tsuji J. Tetrahedron 1969, 25: 4099 - 14
Ballini R.Bosica G.Fiorini D.Righi P. Synthesis 2002, 681 ; and references cited therein -
15a
Barrett AGM.Broughton HB. J. Org. Chem. 1984, 49: 3673 -
15b
Barrett AGM.Broughton HB. J. Org. Chem. 1986, 51: 495 - 16
Hedaya E.Theodoropulos S. Tetrahedron 1968, 24: 2241 - 17
Amos RA.Katzenellenbogen JA. J. Org. Chem. 1978, 43: 560 - 18
Seki K.Sasaki T.Wano S.Haga K.Kaneko R. Phytochemistry 1995, 40: 1175 - 19
Reddy PY.Kondo S.Toru T.Ueno Y. J. Org. Chem. 1997, 62: 2652
References
NCL Communication No. 6632.