Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York An Easy Access to (E)-Alkylidenesuccinic Acids [1] Sivaprakasam Mangaleswaran, Narshinha P. Argade*Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, IndiaFax: +91(20)5893153; e-Mail: argade@dalton.ncl.res.in; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References1 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
