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Synlett 2013; 24(13): 1671-1674
DOI: 10.1055/s-0033-1339308
DOI: 10.1055/s-0033-1339308
letter
NHC-Catalyzed Annulation of Enals to 2,4-Dien-1-ones: Efficient Diastereoselective Synthesis of 1,3-Diaryl-4-styrenyl Cyclopentenes
Further Information
Publication History
Received: 10 May 2013
Accepted after revision: 01 June 2013
Publication Date:
17 July 2013 (online)
Abstract
Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation strategy has been utilized for the efficient synthesis of styrenyl-substituted cyclopentenes from 2,4-dienones.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
- 1a Pellissier H. Tetrahedron 2007; 63: 9267
- 1b Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
- 1c MacMillan DW. C. Nature (London) 2008; 455: 304
-
2 Breslow R. J. Am. Chem. Soc. 1958; 80: 3719
-
3a Stetter H, Schreckenberg M. Angew. Chem., Int. Ed. Engl. 1973; 12: 81
- 3b Stetter H. Angew. Chem., Int. Ed. Engl. 1976; 15: 639
- 4a Christmann M. Angew. Chem. Int. Ed. 2005; 44: 2632
-
4b Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
- 4c Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
-
4d Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
- 4e Moore JL, Rovis T. Top. Curr. Chem. 2011; 291: 77
- 4f Phillips EM, Chan A, Scheidt KA. Aldrichimica Acta 2009; 42: 55
- 4g Chiang P.-C, Bode JW In N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools . The Royal Society of Chemistry; Cambridge: 2011: 399
-
5 Burstein C, Glorius F. Angew. Chem. Int. Ed. 2004; 43: 6205
-
6 Sohn SS, Rosen EL, Bode JW. J. Am. Chem. Soc. 2004; 126: 14370
- 7a Nair V, Vellalath S, Poonoth M, Mohan R, Suresh E. Org. Lett. 2006; 8: 507
- 7b Nair V, Vellalath S, Poonoth M, Suresh E, Viji S. Synthesis 2007; 3195
- 8a He M, Bode JW. Org. Lett. 2005; 7: 3131
- 8b Zhang B, Feng P, Sun L.-H, Cui Y, Ye S, Jiao N. Chem. Eur. J. 2012; 18: 9198
-
9a Nair V, Vellalath S, Poonoth M, Suresh E. J. Am. Chem. Soc. 2006; 128: 8736
-
9b Chiang P.-C, Kaeobamrung J, Bode JW. J. Am. Chem. Soc. 2007; 129: 3520
- 9c Wadamoto M, Phillips EM, Reynolds TE, Scheidt KA. J. Am. Chem. Soc. 2007; 129: 10098
- 9d Cardinal-David B, Raup DE. A, Scheidt KA. J. Am. Chem. Soc. 2010; 132: 5345
- 9e Cohen DT, Cardinal-David B, Roberts JM, Sarjeant AA, Scheidt KA. Org. Lett. 2011; 13: 1068
- 9f Nair V, Paul RR, Padmaja DV. M, Aiswarya N, Sinu CR, Jose A. Tetrahedron 2011; 67: 9885
- 9g Paul RR, Lakshmi KC. S, Suresh E, Nair V. Tetrahedron Lett. 2013; 54: 2046
- 10 Chan A, Scheidt KA. J. Am. Chem. Soc. 2008; 130: 2740
- 11 Nair V, Babu BP, Vellalath S, Varghese V, Raveendran AE, Suresh E. Org. Lett. 2009; 11: 2507
- 12a Nair V, Sinu CR, Babu BP, Varghese V, Jose A, Suresh E. Org. Lett. 2009; 11: 5570
-
12b Maji B, Ji L, Wang S, Vedachalam S, Ganguly R, Liu X.-W. Angew. Chem. Int. Ed. 2012; 51: 8276
- 13a Nair V, Varghese V, Babu BP, Sinu CR, Suresh E. Org. Biomol. Chem. 2010; 8: 761
- 13b He M, Bode JW. J. Am. Chem. Soc. 2008; 130: 418
- 13c Rommel M, Fukuzumi T, Bode JW. J. Am. Chem. Soc. 2008; 130: 17266
- 14a Nair V, Poonoth M, Vellalath S, Suresh E, Thirumalai R. J. Org. Chem. 2006; 71: 8964
- 14b Phillips E, Reynolds T, Scheidt K. J. Am. Chem. Soc. 2008; 130: 2416
- 14c Seayad J, Patra P, Zhang Y, Ying J. Org. Lett. 2008; 10: 953
- 14d Yang L, Tan B, Wang F, Zhong G. J. Org. Chem. 2009; 74: 1744
- 14e Sun L.-H, Shen L.-T, Ye S. Chem. Commun. 2011; 47: 10136
- 14f Nair V, Babu BP, Vellalath S, Eringathodi Suresh E. Chem. Commun. 2008; 747
- 14g Nair V, Paul RR, Lakshmi KC. S, Menon RS, Jose A, Sinu CR. Tetrahedron Lett. 2011; 52: 5992
- 15a Zhao X, DiRocco DA, Rovis T. J. Am. Chem. Soc. 2011; 133: 12466
- 15b Cohen DT, Scheidt KA. Chem. Sci. 2012; 3: 53
- 16a Struble J, Bode JW. Tetrahedron 2009; 65: 4957
- 16b Sinu CR, Padmaja DV. M, Ranjini UP, Seetha Lakshmi KC, Suresh E, Nair V. Org. Lett. 2013; 15: 68
-
17a Domingo L, Zaragozá R, Arnó M. Org. Biomol. Chem. 2010; 8: 4884
- 17b Verma P, Patni PA, Sunoj RB. J. Org. Chem. 2011; 76: 5606
- 18 Synthesis of (E)-1-Methoxy-4-(3-phenyl-5-styrylcyclopent-2-enyl)benzene (3a): 1,5-Diphenylpenta-2,4-dien-1-one (117 mg, 0.5 mmol), 4-methoxycinnamaldehyde (162 mg, 1 mmol) and IMesCl (15 mol%) were taken in a 25-mL round-bottom flask. Into this was added anhyd CH2Cl2 (5 mL) followed by DBU (20 mol%) and the reaction mixture was stirred under an inert atmosphere of argon. The completion of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was subjected to column chromatography on 100–200 mesh silica gel using EtOAc–hexane (2:98) mixture, affording the styryl cyclopentene 3a (85%) as a colorless liquid. Chemical formula: C26H24O. 1H NMR (500 MHz, CDCl3): δ = 7.49 (d, J = 7.9 Hz, 2 H), 7.34 (t, J = 7.7 Hz, 4 H), 7.27 (dd, J = 13.0, 5.8 Hz, 3 H), 7.18 (t, J = 6.0 Hz, 1 H), 7.15 (d, J = 8.1 Hz, 2 H), 6.83 (d, J = 7.9 Hz, 2 H), 6.40 (dd, J = 15.8, 8.2 Hz, 1 H), 6.28 (d, J = 15.8 Hz, 1 H), 6.19 (s, 1 H), 3.85 (d, J = 7.8 Hz, 1 H), 3.79 (s, 3 H), 3.12 (dd, J = 15.2, 8.2 Hz, 1 H), 2.99 (p, J = 8.0 Hz, 1 H), 2.79 (dd, J = 15.2, 7.8 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 158.3, 142.1, 137.5, 136.5, 136.1, 133.0, 129.8, 128.6, 128.5, 128.5, 128.4, 127.4, 127.0, 126.1, 125.7, 113.9, 57.8, 55.1, 53.2, 39.8.
For reviews on NHC-catalyzed reactions, see:
For theoretical calculations involving DFT studies for the formation of cyclopentenes, see: