Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2014; 25(4): 461-465
DOI: 10.1055/s-0033-1340349
DOI: 10.1055/s-0033-1340349
synpacts
A Facile Access to Piperidine Derivatives via Copper(I)-Catalyzed 1,3-Dipolar [6+3] Cycloadditions of Azomethine Ylides with Fulvenes
Further Information
Publication History
Received: 16 September 2013
Accepted after revision: 08 November 2013
Publication Date:
08 January 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201404/lookinside/thumbnails/10.1055-s-0033-1340349-1.jpg)
Abstract
Enantioenriched heterocyclic piperidines are important structural motifs present in numerous natural products and biologically active molecules. This article outlines our recent efforts to develop a straightforward access to highly functionalized piperidine derivatives with multiple stereogenic centers, in good yields and excellent stereoselectivities, via copper(I)/TF-BiphamPhos-catalyzed asymmetric 1,3-dipolar [6+3] cycloadditions of azomethine ylides with fulvenes.
-
References
- 1a Hou X.-L, Yang Z, Yeung K.-S, Wong HN. C In Progress in Heterocyclic Chemistry . Vol. 19. Gribble GW, Joule JA. Pergamon; Oxford: 2008
-
1b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 1c Carruthers W. Cycloaddition Reactions in Organic Synthesis . Pergamon; Oxford: 1990: 1-208
-
2a Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
- 2b Chen Q.-A, Wang D.-S, Zhou Y.-G. Chem. Commun. 2010; 46: 4043
- 2c Nájera C, Sansano JM. Angew. Chem. Int. Ed. 2005; 44: 6272
-
2d Álvarez-Corral M, Muñoz-Dorado M, Rodríguez-García I. Chem. Rev. 2008; 108: 3174
- 2e Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887
- 2f Engels B, Christl M. Angew. Chem. Int. Ed. 2009; 48: 7968
- 2g Adrio J, Carretero JC. Chem. Commun. 2011; 47: 6784
- 3 Schreiber SL. Science 2000; 287: 1964
- 4a 1,3-Dipolar Cycloaddition Chemistry . Padwa A. John Wiley & Sons; New York: 1984
- 4b Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Padwa A, Pearson WH. John Wiley & Sons; New York: 2003
- 5a Han B, He Z.-Q, Li J.-L, Li R, Jiang K, Liu T.-Y, Chen Y.-C. Angew. Chem. Int. Ed. 2009; 48: 5474
- 5b Jiang J, Yu J, Sun X.-X, Rao Q.-Q, Gong L.-Z. Angew. Chem. Int. Ed. 2008; 47: 2458
- 5c Leijondahl K, Boren L, Braun R, Backvall J.-E. Org. Lett. 2008; 10: 2027
- 5d Beng TK, Gawley RE. Org. Lett. 2011; 13: 394
- 5e Gouault N, Le RM, Cheignon A, Uriac P, David M. Org. Lett. 2011; 13: 4371
- 5f Monaco MR, Renzi P, Scarpino SD. M, Bella M. Org. Lett. 2011; 13: 4546
- 6 Nakamura M, Chi Y.-M, Yan W.-M, Yonezawa A, Nakasugi Y, Toyokichi Y, Hashimoto F, Kinjo J, Nohara T, Sakurada S. Planta Med. 2001; 67: 114
- 7 Nakamura M, Kido K, Kinjo J, Nohara T. Phytochemistry 2000; 53: 253
- 8a Che Y.-C, Cochrum RK, Tseng MT, Ghooray DT, Moore JP, Winters SJ, Clark BJ. Biol. Reprod. 2007; 77: 1017
- 8b Hild SA, Marshall GR, Attaridi BJ, Hess RA, Schlatt S, Simorangkir DR, Ramaswamy S, Koduri S, Reel JR, Plant TM. Endocrinology 2007; 148: 1784
- 8c Stefanska AL, Cassels R, Ready SJ, Warr SR. J. Antibiot. 2000; 53: 357
- 9 Hong B.-C, Gupta AK, Wu M.-F, Liao J.-H, Lee G.-H. Org. Lett. 2003; 5: 1689
- 10a Wang C.-J, Liang G, Xue Z.-Y, Gao F. J. Am. Chem. Soc. 2008; 130: 17250
- 10b Xue Z.-Y, Li Q.-H, Tao H.-Y, Wang C.-J. J. Am. Chem. Soc. 2011; 133: 11757
- 10c Liang G, Tong M.-C, Tao H.-Y, Wang C.-J. Adv. Synth. Catal. 2010; 352: 1851
- 10d Liu T.-L, He Z.-L, Tao H.-Y, Cai Y.-P, Wang C.-J. Chem. Commun. 2011; 47: 2616
- 10e Yan D, Li Q, Wang C.-J. Chin. J. Chem. 2012; 30: 2714
- 10f Teng H.-L, Huang H, Wang C.-J. Chem. Eur. J. 2012; 18: 12614
- 10g Liu K, Teng H.-L, Yao L, Tao H.-Y, Wang C.-J. Org. Lett. 2013; 15: 2250
- 11a Potowski M, Bauer JO, Strohmann C, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2012; 51: 9512
- 11b Potowski M, Antonchick AP, Waldmann H. Chem. Commun. 2013; 49: 7800
- 12a He Z.-L, Teng H.-L, Wang C.-J. Angew. Chem. Int. Ed. 2013; 52: 2934
- 12b Part of this research was first presented at the Chiral China 2012 Symposium, Lanzhou, China, August 17–19, 2012.
For recent reviews, see: