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Synlett 2015; 26(02): 142-166
DOI: 10.1055/s-0034-1379251
DOI: 10.1055/s-0034-1379251
account
Phosphine Organocatalysis for the Synthesis of Spirocyclic Compounds
Further Information
Publication History
Received: 21 July 2014
Accepted after revision: 15 September 2014
Publication Date:
17 December 2014 (online)
Abstract
This account describes the use of phosphines as simple organocatalysts that catalyze the synthesis of complex spirocyclic compounds. Besides our own results, coverage of relevant literature in this field is also provided, including asymmetric variants and synthetic applications.
1 Introduction
2 Cycloaddition Reactions Involving Allenoates or 2-Butynoates
2.1 [3+2] Cycloadditions
2.2 [4+2] Cycloadditions
2.3 [4+1] Cycloadditions
3 [3+2] Cycloadditions with Morita–Baylis–Hillman Adducts
4 Cycloaddition Reactions Using Ynone Derivatives
5 Cycloaddition Reactions Involving Methyl Vinyl Ketone
Derivatives
6 Miscellaneous Reactions
7 Conclusions
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References
- 1a Methot JL, Roush WR. Adv. Synth. Catal. 2004; 346: 1035
- 1b Denmark SE, Beutner GL. Angew. Chem. Int. Ed. 2008; 47: 1560
- 1c Ye L.-W, Zhou J, Tang Y. Chem. Soc. Rev. 2008; 37: 1140
- 1d Cowen BJ, Miller SJ. Chem. Soc. Rev. 2009; 38: 3102
- 1e Marinetti A, Voituriez A. Synlett 2010; 174
- 1f Wang Z, Xu X, Kwon O. Chem. Soc. Rev. 2014; 43: 2927
- 2 Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
- 3 Zhang C, Lu X. J. Org. Chem. 1995; 60: 2906
- 5 Xia Y, Liang Y, Chen Y, Wang M, Jiao L, Huang F, Liu S, Li Y, Yu Z.-X. J. Am. Chem. Soc. 2007; 129: 3470
- 6a Dudding T, Kwon O, Mercier E. Org. Lett. 2006; 8: 3643
- 6b Mercier E, Fonovic B, Henry C, Kwon O, Dudding T. Tetrahedron Lett. 2007; 48: 3617
- 6c Liang Y, Liu S, Xia Y, Li Y, Yu Z.-X. Chem. Eur. J. 2008; 14: 4361
- 6d Huang G.-T, Lankau T, Yu C.-H. J. Org. Chem. 2014; 79: 1700
- 7 Du Y, Lu X, Yu Y. J. Org. Chem. 2002; 67: 8901
- 8a Du Y, Lu X. J. Org. Chem. 2003; 68: 6463
- 8b For a review on the use of phosphine-promoted reactions for the synthesis of natural products, see: Gomez C, Betzer J.-F, Voituriez A, Marinetti A. ChemCatChem 2013; 5: 1055
- 9 Cowen BJ, Miller SJ. J. Am. Chem. Soc. 2007; 129: 10988
- 10 Wallace DJ, Sidda RL, Reamer RA. J. Org. Chem. 2007; 72: 1051
- 11 Pham TQ, Pyne SG, Skelton BW, White AH. Tetrahedron Lett. 2002; 43: 5953
- 12 Pham TQ, Pyne SG, Skelton BW, White AH. J. Org. Chem. 2005; 70: 6369
- 13 Fujiwara Y, Fu GC. J. Am. Chem. Soc. 2011; 133: 12293
- 14 For a review on Binepines, see: Gladiali S, Alberico E, Junge K, Beller M. Chem. Soc. Rev. 2011; 40: 3744
- 15a Ung AT, Schafer K, Lindsay KB, Pyne SG, Amornraksa K, Wouters R, Van der Linden I, Biesmans I, Lesage AS. J, Skelton BW, White AH. J. Org. Chem. 2002; 67: 227
- 15b Pyne SG, Schafer K, Skelton BW, White AH. Chem. Commun. 1997; 2267
- 16 Zhou Y.-Q, Li C, Rong J, Yan H, Chen J.-R, Xiao W.-J. Synlett 2011; 1000
- 17 Steurer M, Jensen KL, Worgull D, Jørgensen KA. Chem. Eur. J. 2012; 18: 76
- 18 Wang D, Wei Y, Shi M. Chem. Commun. 2012; 48: 2764
- 19 Wilson JE, Fu GC. Angew. Chem. Int. Ed. 2006; 45: 1426
- 20 Voituriez A, Panossian A, Fleury-Brégeot N, Retailleau P, Marinetti A. J. Am. Chem. Soc. 2008; 130: 14030
- 21 Voituriez A, Panossian A, Fleury-Brégeot N, Retailleau P, Marinetti A. Adv. Synth. Catal. 2009; 351: 1968
- 22 Pinto N, Neel M, Panossian A, Retailleau P, Frison G, Voituriez A, Marinetti A. Chem. Eur. J. 2010; 16: 1033
- 23 Duvvuru D, Pinto N, Gomez C, Betzer J.-F, Retailleau P, Voituriez A, Marinetti A. Adv. Synth. Catal. 2012; 354: 408
- 24a Dimmock JR, Padmanilayam MP, Puthucode RN, Nazarali AJ, Motaganahalli NL, Zello GA, Quail JW, Oloo EO, Kraatz H.-B, Prisciak JS, Allen TM, Santos CL, Balzarini J, De Clercq E, Manavathu EK. J. Med. Chem. 2001; 44: 586
- 24b Suresh Kumar S, Perumal S, Arun Shetty K, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2010; 45: 124
- 25a Fernández I, Khiar N. Chem. Rev. 2003; 103: 3651
- 25b Pellissier H. Tetrahedron 2007; 63: 1297
- 25c Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
- 25d McGarrigle EM, Myers EL, Illa O, Shaw MA, Riches SL, Aggarwal VK. Chem. Rev. 2007; 107: 5841
- 25e Carreño MC, Hernández-Torres G, Ribagorda M, Urbano A. Chem. Commun. 2009; 6129
- 26 Pinto N, Retailleau P, Voituriez A, Marinetti A. Chem. Commun. 2011; 47: 1015
- 27a Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 27b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
- 27c Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
- 27d Cheng D, Ishihara Y, Tan B, Barbas CF. III. ACS Catal. 2014; 4: 743
- 28 Voituriez A, Pinto N, Neel M, Retailleau P, Marinetti A. Chem. Eur. J. 2010; 16: 12541
- 29 Gomez C, Gicquel M, Carry J.-C, Schio L, Retailleau P, Voituriez A, Marinetti A. J. Org. Chem. 2013; 78: 1488
- 30 Sampath M, Loh T.-P. Chem. Sci. 2010; 1: 739
- 31 Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J. Am. Chem. Soc. 2005; 127: 10130
- 32 Zhao Y, Liu L, Sun W, Lu J, McEachern D, Li X, Yu S, Bernard D, Ochsenbein P, Ferey V, Carry J.-C, Deschamps JR, Sun D, Wang S. J. Am. Chem. Soc. 2013; 135: 7223
-
33 Zhang X.-C, Cao S.-H, Wei Y, Shi M. Chem. Commun. 2011; 47: 1548
- 34 Zhang X.-C, Cao S.-H, Wei Y, Shi M. Org. Lett. 2011; 13: 1142
- 35 Guo S, Wang R, Li J, Li C, Deng H, Jia X. Synlett 2011; 2256
- 36 Li X, Wang F, Dong N, Cheng J.-P. Org. Biomol. Chem. 2013; 11: 1451
- 37 Gicquel M, Gomez C, Retailleau P, Voituriez A, Marinetti A. Org. Lett. 2013; 15: 4002
- 38 Li E, Huang Y, Liang L, Xie P. Org. Lett. 2013; 15: 3138
- 39 Tran YS, Kwon O. J. Am. Chem. Soc. 2007; 129: 12632
- 40 Zhong F, Han X, Wang Y, Lu Y. Chem. Sci. 2012; 3: 1231
- 41 Han X, Yao W, Wang T, Tan YR, Yan Z, Kwiatkowski J, Lu Y. Angew. Chem. Int. Ed. 2014; 53: 5643
- 42 Du Y, Lu X, Zhang C. Angew. Chem. Int. Ed. 2003; 42: 1035
- 43 Deng H.-P, Wei Y, Shi M. Org. Lett. 2011; 13: 3348
- 44 Zhong F, Han X, Wang Y, Lu Y. Angew. Chem. Int. Ed. 2011; 50: 7837
- 45 Tan B, Candeias NR, Barbas CF. III. J. Am. Chem. Soc. 2011; 133: 4672
- 46 Albertshofer K, Tan B, Barbas CF. III. Org. Lett. 2013; 15: 2958
- 47 Hu F, Wei Y, Shi M. Tetrahedron 2012; 68: 7911
- 48 Wang Y, Liu L, Zhang T, Zhong N.-J, Wang D, Chen Y.-J. J. Org. Chem. 2012; 77: 4143
- 49 Lian Z, Shi M. Eur. J. Org. Chem. 2012; 581
- 50 Lian Z, Shi M. Org. Biomol. Chem. 2012; 10: 8048
- 51 Yang L, Xie P, Li E, Li X, Huang Y, Chen R. Org. Biomol. Chem. 2012; 10: 7628
- 52 Lian Z, Wei Y, Shi M. Tetrahedron 2012; 68: 2401
- 53 Zhou Q.-F, Chu X.-P, Ge F.-F, Li C, Lu T. Mol. Diversity 2013; 17: 563
- 54 Ramachary DB, Venkaiah C, Krishna PM. Org. Lett. 2013; 15: 4714
- 55 Liang L, Li E, Xie P, Huang Y. Chem. Asian. J. 2014; 9: 1270
- 56 Hu F.-L, Wei Y, Shi M. Adv. Synth. Catal. 2014; 356: 736
- 57 Zhang X.-N, Chen G.-Q, Dong X, Wei Y, Shi M. Adv. Synth. Catal. 2013; 355: 3351
- 58 Zhang X.-N, Dong X, Wei Y, Shi M. Tetrahedron 2014; 70: 2838
- 59 Selvakumar K, Vaithiyanathan V, Shanmugam P. Chem. Commun. 2010; 46: 2826
- 60 Hu C, Zhang Q, Huang Y. Chem. Asian J. 2013; 8: 1981
For reviews on the synthesis of spirooxindoles, see: