Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A New Synthesis of exo-Methylene Butyrolactones from Nitroalkanes Roberto Ballini*, Giovanna Bosica, Damiana LiviDipartimento di Scienze Chimiche dell’Università, Via S. Agostino 1, 62032 Camerino (MC), ItalyFax: +39(737)637345; e-Mail: ballini@camserv.unicam.it; Recommend Article Abstract Buy Article All articles of this category Abstract A versatile route to exo-methylene butyrolactones was developed by employing a three step reaction sequence consisting of Michael addition of primary nitroalkanes 1 to ethyl (2-bromomethyl)acrylate (2), then Nef conversion of the nitro derivatives 3, and subsequent lactonization of the obtained keto esters 4. The method is chemoselective for important functionalities such as ester, C=C double bond and hydroxyl. Key words nitro compounds - Michael addition - lactones - Nef reaction - elimination Full Text References References 1a Mori K. Tetrahedron 1988, 45: 3233 1b Dubs P. Stussi R. Helv. Chim. Acta 1978, 61: 990 1c Kano S. Shibuya S. Ebata T. Heterocycles 1980, 14: 661 2a Sharpless KB. Lauer RF. Teranishi AY. J. Am. Chem. Soc. 1973, 95: 6137 2b Trost BM. Salzmann TN. Hiroi K. J. Am. Chem. Soc. 1976, 98: 4887 2c Grimm EL. Reissig H.-U. J. Org. Chem. 1985, 50: 242 2d Koch SSC. Chamberlin AR. J. Org. Chem. 1993, 58: 2725 3a Carlson RM. Yang Q. Tetrahedron Lett. 1994, 35: 7919 3b Lu X. Wang Z. Ji J. Tetrahedron Lett. 1994, 35: 613 3c Dulcere J.-P. Mihabi MN. Rodriguez J. J. Org. Chem. 1993, 58: 5709 3d Lu X. Zhu G. Synlett 1993, 68 3e Petragnani N. Ferraz HMC. Silva GVJ. Synthesis 1986, 157 3f Grieco PA. Synthesis 1975, 67 3g Martin VS. Rodriguez CM. Martin T. Org. Prep. Proced. Int. 1998, 30: 291 4a Kupchan SM. Britto RW. Ziegler MP. Gilmore CJ. Restivo RG. Bryan RF. J. Am. Chem. Soc. 1973, 95: 1335 4b Amos RA. Katzenellenbogen J. J. Org. Chem. 1978, 43: 560 4c Yamamoto M. J. Chem. Soc., Perkin Trans. 1 1981, 582 4d Jellal A. Grimaldi J. Santelli M. Tetrahedron Lett. 1984, 25: 3179 4e Gollin I. J. Chem. Soc., Perkin Trans. 1 1998, 1869 4f Hoffman HMR. Rabe J. Angew. Chem. Int. Ed. Engl. 1985, 24: 94 4g Mulzer J. In Comprehensive Organic Synthesis Vol. 6: Fleming I. Trost BM. Pergamon; Oxford: 1991. p.323 5a Andrews RC. Marhall JA. DeHoff BS. Synth. Commun. 1986, 16: 1953 5b Patterson JW. Mc Murry J. J. Chem. Soc., Chem. Commun. 1971, 488 5c Chan DMT. Marder TB. Milstein D. Taylor NJ. J. Am. Chem. Soc. 1987, 109: 6385 5d Bryan VJ. Chan T.-H. Tetrahedron Lett. 1996, 37: 5341 5e Tamaru Y. Hojo M. Yoshida Z. J. Org. Chem. 1991, 56: 1099 5f Rosini G. Laffi F. Marotta E. Pagani I. Righi P. J. Org. Chem. 1998, 62: 2398 5g Leroy B. Dumeunier R. Markò IE. Tetrahedron Lett. 2000, 41: 10215 6 Lee C.-W. Gil JM. Oh DY. Heterocycles 1997, 45: 943 7a Buechel KL. Roechling H. Korte F. Liebigs Ann. Chem. 1965, 685: 10 7b Jackson JA. Hammond GB. Wiemer DF. J. Org. Chem. 1989, 54: 4759 8 Ballini R. Marcantoni E. Perella S. J. Org. Chem. 1999, 64: 2954 9a Rosini G. Ballini R. Synthesis 1988, 833 9b Rosini G. Ballini R. Petrini M. Marotta E. Righi P. Org. Prep. Proced. Int. 1990, 22: 707 9c Ballini R. In Studies in Natural Products Chemistry Vol. 19: Atta-ur-Rahman, Ed.; Elsevier; Amsterdam: 1997. p.117 9d Ballini R. Bosica G. In Recent Research Development in Organic Chemistry Vol. 1: Transworld Research Network; Trivandum: 1997. p.11 9e Ballini R. Synlett 1999, 1009 10a Chamakh A. M’hirsi M. Villiéras J. Lebreton J. Amri H. Synthesis 2000, 295 10b Pinnick HK. Org. React. 1990, 38: 655
