Solvent-Free Organocatalytic Mukaiyama-Michael Addition of 2-Trimethylsilyloxy Furan to Nitroalkenes Catalyzed by Brønsted Acids

Abstract

The first organocatalytic Mukaiyama-Michael addition of 2-trimethylsilyloxy furan to nitroalkenes was promoted by Brønsted acids under solvent-free conditions. The conjugate addition took place in moderate to good yields with variously substituted nitroalkenes. The procedure is operationally simple and no workup is required.

Key words

solvent-free - conjugate addition - Brønsted acids - ­nitroalkenes - 2-trimethylsilyloxy furan

References and Notes

• For reviews, see:
• 1a Rao YS. Chem. Rev.  1976,  76:  625 
• 1b De Souza MVN. Mini-Rev. Org. Chem.  2005,  2:  139 
• 1c Carter NB. Nadany AE. Sweeney JB. J. Chem. Soc., Perkin Trans. 1  2002,  2324 
• 2 Jefford CW. Sledeski AW. Boukouvalas J. Helv. Chim. Acta  1989,  72:  1362 
• 3a Figadere B. Chaboche C. Peyrat JF. Cave A. Tetrahedron Lett.  1993,  34:  8093 
• 3b Figadere B. Peyrat JF. Cave A. J. Org. Chem.  1997,  62:  3428 
• 3c Hanessian S. Grillo TA. J. Org. Chem.  1998,  63:  1049 
• 3d Hanessian S. Giroux S. Buffat M. Org. Lett.  2005,  7:  3989 
• 3e Hanna I. Ricard L. Tetrahedron Lett.  1999,  40:  863 
• 3f Cho C.-W. Prische MJ. Angew. Chem. Int. Ed.  2004,  6689 
• 3g Maulide N. Marko IE. Org. Lett.  2006,  8:  3705 
• 4 Kang S.-K. Yamaguchi T. Ho P.-S. Kim W.-Y. Yoon S.-K. Tetrahedron Lett.  1997,  38:  1947 
• 5 Kang S.-K. Ryu H.-C. Hong Y.-T. J. Chem. Soc., Perkin Trans. 1  2000,  20:  3350 
• 6 For a review containing these topics, see: Casiraghi G. Zanardi F. Appendino G. Rassu G. Chem. Rev.  2000,  100:  1929 
• For selected recent applications, see:
• 7a Szlosek M. Figadere B. Angew. Chem. Int. Ed.  2000,  39:  1799 
• 7b Onitsuka S. Matsuoka Y. Irie R. Katsuki T. Chem. Lett.  2003,  32:  974 
• 7c Palombi L. Acocella MR. Celenta N. Massa A. Villano R. Scettri A. Tetrahedron: Asymmetry  2006,  17:  3300 
• 7d Carswell EL. Snapper ML. Hoveyda AH. Angew. Chem. Int. Ed.  2006,  45:  7230 
• 7e De Rosa M. Citro L. Soriente A. Tetrahedron Lett.  2006,  47:  8507 
• 8a Brimble MA. Elliot RJR. Tetrahedron  1997,  53:  7715 
• 8b Carreno MC. Luzon CG. Ribagorda M. Chem. Eur. J.  2002,  8:  208 
• 8c Suga H. Kitamura T. Kakehi A. Baba T. Chem. Commun.  2004,  1414 
• 8d Kitajima H. Katsuki T. Synlett  1997,  568 
• 8e Kitajima H. Katsuki T. Tetrahedron  1997,  53:  17015 
• 8f Desimoni G. Faita G. Filippone S. Mella M. Zampori MG. Zema M. Tetrahedron  2001,  57:  10203 
• 8g Desimoni G. Faita G. Guala M. Laurenti A. Mella M. Chem. Eur. J.  2005,  11:  3816 
• 9 Fukuyama T. Goto S. Tetrahedron Lett.  1989,  30:  6491 
• 10 Brown SP. Goodwin NC. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  1192 
• 11 Trost BM. Hitce J. J. Am. Chem. Soc.  2009,  131:  4572 
• 12 For a review, see: Ballini R. Petrini M. Tetrahedron  2004,  60:  1017 
• 13 Kamlet MJ. Kaplan LA. Dacons JC. J. Org. Chem.  1961,  26:  4371 
• 14a Beck K. Seebach D. Chem. Ber.  1991,  124:  2897 
• 14b Loyd DH. Nichols DE. J. Org. Chem.  1986,  51:  4294 
• 14c Barrett AGM. Spilling CD. Tetrahedron Lett.  1988,  29:  5733 
• 14d Poupart MA. Fazal G. Goulet S. Mat LT. J. Org. Chem.  1999,  64:  1356 
• 15 Tamura R. Kamimura A. Ono N. Synthesis  1991,  423 
• 16a Martin NJA. Cheng X. List B. J. Am. Chem. Soc.  2008,  130:  13862 
• 16b Martin NJA. Ozores L. List B.
  J. Am. Chem. Soc.  2007,  129:  8976 
• 16c Itoh J. Fuchibe K. Akiyama T. Angew. Chem. Int. Ed.  2008,  47:  4016 
• 16d Schreiner PR. Zhang Z. Synthesis  2007,  2559 
• For reviews, see:
• 17a Connon SJ. Angew. Chem. Int. Ed.  2006,  45:  3909 
• 17b Akiyama T. Chem. Rev.  2007,  107:  5744 
• 17c Terada M. Chem. Commun.  2008,  4097 

18

General Procedure
The reaction was carried out in a dry vial. Nitrostyrene (149 mg, 1.0mmol) and 2-trimethylsilyloxy furan (200 µL, 1.2 mmol) were added to the catalyst (5 mol%) at -20 ˚C. The reaction mixture was stirred at the same temperature for
the time indicated. The crude was purified by column chromatography on silica gel in gradient elution with PE-EtOAc to obtain the pure product.