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-00000084.xml
Synthesis 2014; 46(16): 2133-2142
DOI: 10.1055/s-0034-1378392
DOI: 10.1055/s-0034-1378392
feature article
Product Selectivity Control in the Domino Cyclization of 2-(2-Alkynylarylidene)-1,3-dicarbonyl Compounds Catalyzed by Metal Lewis Acids
Further Information
Publication History
Received: 21 May 2014
Accepted after revision: 23 June 2014
Publication Date:
08 July 2014 (online)
Abstract
The selective synthesis of different products from the same kind of starting materials is an attractive, but challenging, task for chemists. This article reports our design for the selective domino reactions of 2-(2-alkynylarylidene)-1,3-dicarbonyl compounds which can be prepared from o-alkynylbenzaldehyde and 1,3-dicarbonyl compounds. Several different types of polycyclic skeletons can be constructed from 2-(2-alkynylarylidene)-1,3-dicarbonyl compounds with by simple subtle modification of the structure or choice of reaction conditions.
-
References
- 1a Ma S, Zhang J. Angew. Chem. Int. Ed. 2003; 42: 183
- 1b Ma S, Zhang J. J. Am. Chem. Soc. 2003; 125: 12386
- 1c Ma S, Lu L, Zhang J. J. Am. Chem. Soc. 2004; 126: 9645
- 1d Kamijo S, Kanazawa C, Yamamoyo Y. J. Am. Chem. Soc. 2005; 127: 9260
- 1e Alcaide B, Almendros P, Martínez del Campo T. Angew. Chem. Int. Ed. 2007; 46: 6684
- 1f Chuprakov S, Gevorgyan V. Org. Lett. 2007; 9: 4463
- 1g Dudnik AS, Sromek AW, Rubina M, Kim JT, Kel’in AV, Gevorgyan V. J. Am. Chem. Soc. 2008; 130: 1440
- 1h Xiao Y, Zhang J. Chem. Commun. 2009; 3594
- 1i Zhang Y, Liu F, Zhang J. Chem. Eur. J. 2010; 16: 6146
- 1j Zhou G, Zhang J. Chem. Commun. 2010; 46: 6593
- 1k Zeng Q, Zhang L, Yang J, Xu B, Xiao Y, Zhang J. Chem. Commun. 2014; 50: 4203
- 1l Wang T, Shi S, Vilhelmsen MH, Zhang T, Rudolph M, Rominger F, Hashmi AS. K. Chem. Eur. J. 2013; 19: 12512
- 1m Gupta S, Koley D, Ravikumar K, Kundu B. J. Org. Chem. 2013; 78: 8624
- 1n Chen Z, Tian Z, Zhang J, Ma J, Zhang J. Chem. Eur. J. 2012; 18: 8591
- 2a Liu L, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 6093
- 2b Liu L, Wei L, Zhang J. Adv. Synth. Catal. 2010; 352: 1920
- 2c Liu L, Wei L, Lu Y, Zhang J. Chem. Eur. J. 2010; 16: 11813
- 3 Gao H, Zhang J. Adv. Synth. Catal. 2009; 351: 85
- 4a Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
- 4b Tietze LF. Chem. Rev. 1996; 96: 115
- 4c Wasilke J.-C, Obrey SJ, Baler RT, Bazan GC. Chem. Rev. 2005; 105: 1001
- 4d Zhou J. Chem. Asian J. 2010; 5: 422
- 4e Shindoh N, Takemoto Y, Takasu K. Chem. Eur. J. 2009; 15: 12168
- 4f Dondoni A, Massi A. Acc. Chem. Res. 2006; 39: 451
- 4g Dömling A. Chem. Rev. 2006; 106: 17
- 4h D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
- 4i Patil NT, Shinde VS, Gajula B. Org. Biomol. Chem. 2012; 10: 211
- 4j Müller TJ. J In Topics in Organometallic Chemistry . Vol. 19. Müller TJ. J. Springer; Berlin: 2006: 149
- 4k Multi-component Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
- 4l Domino Reactions in Organic Synthesis . Tietze LF, Geriche KM. Wiley-VCH; Weinheim: 2006: 359
- 4m Sebren LJ, Devery III JJ, Stephenson CR. J. ACS Catal. 2014; 4: 703
- 4n Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 5a Hitt DM, O’Connor JM. Chem. Rev. 2011; 111: 7904
- 5b Fischer D, Tomeba H, Pahadi NK, Patil NT, Yamamoto Y. Angew. Chem. Int. Ed. 2007; 46: 4764
- 5c Barluenga J, Andina F, Aznar F, Valdés C. Org. Lett. 2007; 9: 4143
- 5d Shibata T, Ueno Y, Kanda K. Synlett 2006; 411
- 5e Shen H.-C, Tang J.-M, Chang H.-K, Yang C.-W, Liu R.-S. J. Org. Chem. 2005; 70: 10113
- 5f Madhushaw RJ, Lo C.-Y, Hwang C.-W, Su M.-D, Shen H.-C, Pal S, Shaikh IR, Liu R.-S. J. Am. Chem. Soc. 2004; 126: 15560
- 5g Shen H.-C, Pal S, Lian J.-J, Liu R.-S. J. Am. Chem. Soc. 2003; 125: 15762
- 5h Lian J.-J, Lin C.-C, Chang H.-K, Chen P.-C, Liu R.-S. J. Am. Chem. Soc. 2006; 128: 9661
- 5i Gao K, Wu J. Org. Lett. 2008; 10: 2251
- 6a Frontier AJ, Collison C. Tetrahedron 2005; 61: 7577
- 6b Tius MA. Eur. J. Org. Chem. 2005; 2193
- 6c Habermas KL, Denmark SE, Jones TK. Org. React. 1994; 45: 1
- 6d Vaidya T, Eisenberg R, Frontier AJ. ChemCatChem 2011; 3: 1531
- 6e Malona JA, Cariou K, Frontier AJ. J. Am. Chem. Soc. 2009; 131: 7560
- 6f He W, Sun X, Frontier AJ. J. Am. Chem. Soc. 2003; 125: 14278
- 6g Janka M, He W, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2004; 126: 6864
- 6h Liang G, Xu Y, Seiple IB, Trauner D. J. Am. Chem. Soc. 2006; 128: 11022
- 6i Lemière G, Gandon V, Cariou K, Hours A, Fukuyama T, Dhimane A.-L, Fensterbank L, Malacria M. J. Am. Chem. Soc. 2009; 131: 2993
- 6j Rueping M, Ieawsuwan W, Antonchick AP, Nachtsheim BJ. Angew. Chem. Int. Ed. 2007; 46: 2097
- 6k Lee JH, Toste FD. Angew. Chem. Int. Ed. 2007; 46: 912
- 6l Janka M, He W, Haedicke IE, Fronczek FR, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2006; 128: 5312
- 6m Fujiwara M, Kawatsura M, Hayase S, Nanjo M, Itoh T. Adv. Synth. Catal. 2009; 351: 123
- 7a Le Conia JM, Perchec P. Synthesis 1975; 1
- 7b Itoh Y, Tsuji H, Yamagata K.-i, Endo K, Tanaka I, Nakamura M, Nakamura E. J. Am. Chem. Soc. 2008; 130: 17161
- 7c Corkey BK, Toste FD. J. Am. Chem. Soc. 2005; 127: 17168
- 7d Kennedy-Smith JJ, Staben ST, Toste FD. J. Am. Chem. Soc. 2004; 126: 4526
- 7e Yang T, Ferrali A, Sladojevich F, Campbell L, Dixon DJ. J. Am. Chem. Soc. 2009; 131: 9140
- 7f Deng C.-L, Song R.-J, Liu Y.-L, Li J.-H. Adv. Synth. Catal. 2009; 351: 3096
- 7g Ito H, Makida Y, Ochida A, Ohmiya H, Sawamura M. Org. Lett. 2008; 10: 5051
- 7h Gao Q, Zheng B.-F, Li J.-H, Yang D. Org. Lett. 2005; 7: 2185
- 8a Viswanathan GS, Wang M, Li C.-J. Angew. Chem. Int. Ed. 2002; 41: 2138
- 8b Kabalka GW, Ju Y, Wu Z. J. Org. Chem. 2003; 68: 7915
- 8c Saito A, Kasai J, Odaira Y, Fukaya H, Hanzawa Y. J. Org. Chem. 2009; 74: 5644
- 8d Balamurugan R, Gudla V. Org. Lett. 2009; 11: 3116
- 9a Rhee JU, Krische MJ. Org. Lett. 2005; 7: 2493
- 9b Jin T, Yamamoto Y. Org. Lett. 2007; 9: 5259
- 9c Jin T, Yamamoto Y. Org. Lett. 2008; 10: 3137
- 9d Jin T, Yang F, Liu C, Yamamoto Y. Chem. Commun. 2009; 3533
- 9e González-Rodríguez C, Escalante L, Varela JA, Castedo L, Saá C. Org. Lett. 2009; 11: 1531
For selected examples, see:
For selected reviews and, see:
For selected reviews, see:
For recent selected examples on the cyclization of o-ethynylphenylalkenes, see:
For example on the cyclization of 2-(2-alkynylarylidene)malonates, see:
For selected reviews on the Nazarov cyclization, see:
For selected representative examples of Nazarov reactions and their applications in total synthesis, see:
For examples of tandem Nazarov cyclization/Michael addition reaction, see:
For a review on the Conia-ene reactions, see:
For selected representative examples of Conia-ene type reactions and its applicance in total synthesis, see:
For some selected recent examples, see: