Synthesis of Cyclopropanated 7-Azabenzonorbornadienes

Abstract

7-Azabenzonorbornadienes bearing various aryl or N-substituents were treated with diazomethane in the presence of palladium to afford desirable yields of cyclopropanated products (75–98%). The current approach suggests an efficient synthesis for CH₂-cyclopropanated 7-azabenzonorbornadienes which lends promise to the development of new ring-opening preparations of biologically useful organic frameworks.

Key words

7-azabenzonorbornadiene - cyclopropanation - diazo compounds - diastereoselectivity - palladium catalysis

• References

• 1 Chen DY, Pouwer RH, Richard J.-A. Chem. Soc. Rev. 2012; 41: 4631
• 2 Kovalenko VN, Mineeva IV. Russ. J. Org. Chem. 2014; 50: 934
• 3 de Nanteuil F, De Simone F, Frei R, Benfatti F, Serrano E, Waser J. Chem. Commun. 2014; 50: 10912
• 4 Lebel H, Marcoux J.-F, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
• 5 Komsta Z, Mayes BA, Moussa A, Shelbourne M, Stewart A, Tyrrell AJ, Wallis LL, Weymouth-Wilson AC, Yurek-George A. Org. Lett. 2014; 16: 4878
• 6 Emerzian MA, Davenport W, Song J, Li J, Erden I. Adv. Synth. Catal. 2009; 351: 999
• 7 Ji C, Miller MJ. Tetrahedron Lett. 2010; 51: 3789
• 8 Sander M, Dehmolow EV, Neuma B, Stammler H.-G. Tetrahedron 1999; 55: 13395
• 9 McKee M, Haner J, Carlson E, Tam W. Synthesis 2014; 46: 1518
• 10a Carlson E, Duret G, Blanchard N, Tam W. Synth. Commun. 2016; 46: 55
• 10b Lough AJ, Carlson E, Tam W. IUCrData 2016; 1: x160341
• 11 Mo D.-L, Yuan T, Ding C.-H, Dai L.-X, Hou X.-L. J. Org. Chem. 2013; 78: 11470
• 12 Tenaglia A, Marc S. J. Org. Chem. 2006; 71: 3569
• 13 Villeneuve K, Tam W. Organometallics 2006; 25: 843
• 14 Kaupp G, Perreten J, Leute R, Prinzbach H. Chem. Ber. 1970; 103: 2288
• 15 De Meijere A. Angew. Chem., Int. Ed. Engl. 1979; 18: 809
• 16 Rayabarapu DK, Cheng C.-H. Acc. Chem. Res. 2007; 40: 971
• 17 Lautens M, Fagnou K, Heibert S. Acc. Chem. Res. 2003; 36: 48
• 18 Woo S, Keay BA. Synthesis 1996; 669
• 19 Chiu P, Lautens M. Top. Curr. Chem. 1997; 190: 1
• 20 Wolthuis E, Jagt DV, Mels S, De Boer A. J. Org. Chem. 1965; 30: 190
• 21 Raheem MA, Edmunds M, Tam W. Can. J. Chem. 2014; 92: 888
• 22 Carlson E, Haner J, McKee M, Tam W. Org. Lett. 2014; 16: 1776
• 23 Tigchelaar A, Haner J, Carlson E, Tam W. Synlett 2014; 25: 2355
• 24 Simmons HE, Smith RD. J. Am. Chem. Soc. 1959; 81: 4256
• 25 Stenstrøm Y. Synth. Commun. 1992; 22: 2801
• 26a Furukawa J, Kawabata N, Nishimura J. Tetrahedron 1968; 24: 53
• 26b Furukawa J, Kawabata N, Nishimura J. Tetrahedron Lett. 1966; 28: 3353
• 27 Wittig G, Schwarzenbach K. Justus Liebigs Ann. Chem. 1961; 650: 1
• 28 Long Y, Yang D, Zeng H, Xie L, Wu L, Mo H, Zuo X. Chin. J. Chem. 2010; 28: 235
• 29 Shendage DM, Fröhlich R, Haufe G. Org. Lett. 2004; 6: 3675
• 30 Lautens M, Fagnou K, Zunic V. Org. Lett. 2002; 4: 3465
• 31 Hodgson DM, Bebbington MW. P, Willis P. Org. Biomol. Chem. 2003; 1: 3787
• 32 Sun CH, Yang CZ, Shih SY, Lin KS. Bull. Inst. Chem., Acad. Sin. 1991; 38: 37
• 33 Ashton PR, Girreser U, Giuffrida D, Kohnke FH, Mathias JP, Raymo FM, Slawin AM, Stoddart JF, Williams DJ. J. Am. Chem. Soc. 1993; 115: 5422
• 34 Cho Y.-H, Fayol A, Lautens M. Tetrahedron: Asymmetry 2006; 17: 416
• 35 Zhang Y, Wang J. Eur. J. Org. Chem. 2011; 1015
• 36 Straub BF. J. Am. Chem. Soc. 2002; 124: 14195
• 37 Still WC, Kahn M, Mitra A. J. Org. Chem. 1978; 43: 2923