Iridium-Catalyzed Anti-Stereoselective Ring-Opening Reactions of Azabicyclic Alkenes with Fluoroalkylamines

Abstract

A novel iridium-catalyzed ring-opening reaction of azabicyclic alkenes with a variety of fluoroalkylamines was developed. The reaction gave a series of fluorinated trans-1,2-diamine derivatives in good to excellent yields (up to 98%) under relatively mild conditions. The effects of various ligands, catalyst loading, solvents, and temperatures on the yield of the reaction were also investigated. This is the first time that fluorinated compounds were synthesized by incorporating a series of fluoroalkylamines into hydronaphthalene skeleton.

Key words

iridium catalyst - fluoroalkylamines - azabicyclic alkenes - ring-opening reaction - fluorinated trans-1,2-diamines

• References


For reviews, see:
• 1a Ward RS. Chem. Soc. Rev. 1990; 19: 1
• 1b Lautens M. Synthesis 1993; 177
• 1c Lautens M, Fagnou K, Hiebert S. Acc. Chem. Res. 2003; 36: 48
• 1d Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
• 1e Fagnou K, Lautens M. Chem. Rev. 2003; 103: 169
• 1f Rayabarapu DK, Cheng C.-H. Acc. Chem. Res. 2007; 40: 971
• 1g Drusan M, Šebesta R. Tetrahedron 2014; 70: 759
• 1h Yang D.-Q, Han Y.-F. Chin. J. Org. Chem. 2006; 26: 1613
• 1i Cheng H.-C, Liang X.-L, Li X.-L, Long Y.-H, Yang D.-Q. Chin. J. Org. Chem. 2012; 32: 433
• 1j Wu R.-H, Yang W, Cheng G, Li Y, Yang D.-Q. Chin. J. Org. Chem. 2016; 36: 2368

For reviews, see:
• 2a Costello GF, James R, Shaw JS, Slater AM, Stutchbury NC. J. Med. Chem. 1991; 34: 181
• 2b Snyder SE, Aviles-Garay FA, Chakraborti R, Nichols DE, Watts VJ, Mailman RB. J. Med. Chem. 1995; 38: 2395
• 2c Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V, Fiorentini F, Olgiati V, Ghiglieri A, Govoni S. J. Med. Chem. 1995; 38: 942
• 2d Kim K, Guo Y, Sulikowski GA. J. Org. Chem. 1995; 60: 6866
• 3 Nakamura M, Matsuo K, Inoue T, Nakamura E. Org. Lett. 2003; 5: 1373
• 4a Lautens M, Rovis T. J. Am. Chem. Soc. 1997; 119: 11090
• 4b Ma S.-H, Lautens M. J. Org. Chem. 1996; 61: 7246
• 4c Rayabarapu DK, Chiou C.-F, Cheng C.-H. Org. Lett. 2002; 4: 1679
• 4d Zeng Z.-Y, Yang D.-Q, Long Y.-H, Pan X.-J, Huang G.-B, Zuo X.-J, Zhou W. J. Org. Chem. 2014; 79: 5249
• 4e Feng C.-C, Nandi M, Sambaiah T, Cheng C.-H. J. Org. Chem. 1999; 64: 3538
• 5a Bos PH, Rudolph A, Pérez M, Martín FM, Harutyunyan SR, Feringa BL. Chem. Commun. 2012; 48: 1748
• 5b Millet R, Bernardez T, Palais L, Alexakis A. Tetrahedron Lett. 2009; 50: 3474
• 5c Bertozzi F, Pineschi M, Macchia F, Arnold LA, Minnaard AJ, Feringa BL. Org. Lett. 2002; 4: 2703
• 5d Arrayas RG, Cabrera S, Carretero JC. Org. Lett. 2005; 7: 219
• 5e Pineschi M, Del Moro F, Crotti P, Macchia F. Org. Lett. 2005; 7: 3605
• 6 Millward DB, Sammis G, Waymouth RM. J. Org. Chem. 2000; 65: 3902
• 7a Villeneuve K, Tam W. J. Am. Chem. Soc. 2006; 128: 3514
• 7b Burton RR, Tam W. Org. Lett. 2007; 9: 3287
• 7c Tenaglia A, Marc S. J. Org. Chem. 2008; 73: 1397
• 7d Ballantine M, Menard ML, Tam W. J. Org. Chem. 2009; 74: 7570
• 7e Tenaglia A, Marc S, Giordano L, De Riggi I. Angew. Chem. Int. Ed. 2011; 50: 9062
• 8a Lautens M, Fagnou K, Yang D.-Q. J. Am. Chem. Soc. 2003; 125: 14884
• 8b Cho Y.-H, Zunic V, Senboku H, Olsen M, Lautens M. J. Am. Chem. Soc. 2006; 128: 6837
• 8c Zhang L, Le CM, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 5951
• 8d Loh CC. J, Fang X, Peters B, Lautens M. Chem. Eur. J. 2015; 21: 13883
• 8e Loh CC, Schmid M, Peters B, Fang X, Lautens M. Angew. Chem. Int. Ed. 2016; 55: 4600
• 8f Zhu J.-T, Tsui GC, Lautens M. Angew. Chem. Int. Ed. 2012; 51: 12353
• 9a Li L.-P, Rayabarapu DK, Nandi M, Cheng C.-H. Org. Lett. 2003; 5: 1621
• 9b Fan B.-M, Li S.-F, Chen H.-L, Lu Z.-W, Liu S.-S, Yang Q.-G, Yu L, Xu J.-B, Zhou Y.-Y, Wang J. Adv. Synth. Catal. 2013; 355: 2827
• 9c McManus HA, Fleming MJ, Lautens M. Angew. Chem. Int. Ed. 2007; 46: 433
• 9d Lu Z.-W, Wang J, Han B.-Q, Li S.-F, Zhou Y.-Y, Fan B.-M. Adv. Synth. Catal. 2015; 357: 3121
• 9e Li Y, Yang W, Cheng G, Yang D.-Q. J. Org. Chem. 2016; 81: 4744
• 10a Yang D.-Q, Long Y.-H, Wang H, Zhang Z.-M. Org. Lett. 2008; 10: 4723
• 10b Long Y.-H, Yang D.-Q, Zhang Z.-M, Wu Y.-J, Zeng H.-P, Chen Y. J. Org. Chem. 2010; 75: 7291
• 10c Cheng H.-C, Yang D.-Q. J. Org. Chem. 2012; 77: 9756
• 10d Luo R.-S, Liao J.-H, Tang W.-J, Chan AS. C. Chem. Commun. 2013; 49: 9959
• 10e Zeng C.-Y, Yang F, Chen J.-C, Wang J, Fan B.-M. Org. Biomol. Chem. 2015; 13: 8425
• 10f Yang W, Luo R.-S, Yang D.-Q. Molecules 2015; 20: 21103
• 11a Pan X.-J, Huang G.-B, Long Y.-H, Zuo X.-J, Xu X, Gu F.-L, Yang D.-Q. J. Org. Chem. 2014; 79: 187
• 11b Meng L, Yang W, Pan X.-J, Tao M, Cheng G, Wang S.-Y, Zeng H.-P, Long Y.-H, Yang D.-Q. J. Org. Chem. 2015; 80: 2503
• 12 Sawama Y, Kawamoto K, Satake H, Krause N, Kita Y. Synlett 2010; 2151
• 13 Lautens M, Fagnou K, Taylor M, Rovis T. J. Organomet. Chem. 2001; 624: 259
• 14 Leong P, Lautens M. J. Org. Chem. 2004; 69: 2194
• 15 Yang D.-Q, Xia J.-Y, Long Y.-H, Zeng Z.-Y, Zuo X.-J, Wang S.-Y, Li C.-R. Org. Biomol. Chem. 2013; 11: 4871
• 16 Lautens M, Dockendorff C, Fagnou K, Malicki A. Org. Lett. 2002; 4: 1311
• 17 Nishimura T, Tsurumaki E, Kawamoto T, Guo X.-X, Hayashi T. Org. Lett. 2008; 10: 4057
• 18 Henderson JL, Buchwald SL. Org. Lett. 2010; 12: 4442
• 19 Brusoe AT, Hartwig JF. J. Am. Chem. Soc. 2015; 137: 8460
• 20a Arlow SI, Hartwig JF. Angew. Chem. Int. Ed. 2016; 55: 4567
• 20b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 20c Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 20d Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
• 20e Smart BE. J. Fluorine Chem. 2001; 109: 3
• 21a Lautens M, Fagnou K, Zunic V. Org. Lett. 2002; 4: 3465
• 21b Lautens M, Dockendorff C. Org. Lett. 2003; 20: 3695
• 21c Allen A, Marquand PL, Burton R, Villeneuve K, Tam W. J. Org. Chem. 2007; 72: 7849