An organocatalyzed highly regioselective one-pot approach to the synthesis of tetrahydrobenzofuranones

Tetrahedron Letters

Volumn 53, Issue 26, 2012, Pages 3382-3384

  Chawla, Ruchi ^a   Singh, Atul K ^a   Yadav, Lal Dhar S ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

1,3 Cyclohexanediones; Epoxides; Organocatalysis; Regioselective synthesis; Tetrahydrobenzofuranones

Indexed keywords

ENAMINE; FURANONE DERIVATIVE; KETONE; SOLVENT; TETRAHYDROFURAN DERIVATIVE; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS; ORGANIC CHEMISTRY; ORGANOCATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; SCREENING; SOLVENT EFFECT; STEREOCHEMISTRY;

EID: 84861527363     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.04.101     Document Type: Article

References (58)

1. For historical reviews, see: P.W. Hickmott Tetrahedron 38 1975 1982
2. G. Stork Med. Res. Rev. 19 1999 370
3. D. Seebach, A.K. Beck, D.M. Badine, M. Limbach, A. Eschenmoser, A.M. Treasurywala, R. Hobi, W. Prikoszovich, and B. Linder Helv. Chim. Acta 90 2007 425
4. For very recent, representative reviews, see: K.L. Jensen, G. Dickmeiss, H. Jiang, L. Albrecht, and K.A. Jorgensen Acc. Chem. Res. 45 2012 248
5. M. Nielsen, D. Worgull, T. Zweifel, B. Gschwend, S. Bertelsen, and K.A. Jorgensen Chem. Commun. 47 2011 632
6. G. Stork Tetrahedron 67 2011 9754
7. B.M. Trost, and C.S. Brindle Chem. Soc. Rev. 39 2010 1600
8. D. Roca-Lopez, D. Sadaba, I. Delso, R.P. Herrera, T. Tejero, and P. Merino Tetrahedron: Asymmetry 21 2010 2561
9. L.-W. Xu, L. Li, and X.-H. Shi Adv. Synth. Catal. 352 2010 243
10. Also see: M. Wiesner, G. Upert, G. Angelici, and H. Wennemers J. Am. Chem. Soc. 132 2010 6 and Refs. 2,3 therein
11. P.T. Franke, B. Richter, and K.A. Jorgensen Chem. Eur. J. 14 2008 6317
12. G.-S. Liu, Q.-L. Dong, Y.-S. Yao, and Z.-J. Yao Org. Lett. 10 2008 5393
13. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, and A. Ohsawa Org. Lett. 8 2006 1533
14. K. Liu, A. Chougnet, and W.-D. Woggon Angew. Chem. Int. Ed. 47 2008 5827
15. N. Volz, M.C. Bröhmer, M. Nieger, and S. Bräse Synlett 2009 550
16. Y.-J. Zhang, T. Tanaka, Y. Iwamoto, C.-R. Yang, and I. Kouno Tetrahedron Lett. 41 2000 1781
17. T.C. Casey, J. Carlisle, P. Tisseli, L. Male, N. Spencer, and R.S. Grainger J. Org. Chem. 75 2010 7461
18. Q. Liu, Y.-F. Wang, R.-J. Chen, M.-Y. Zhang, Y.-F. Wang, C.-R. Yang, and Y.-J. Zhang J. Nat. Prod. 72 2009 969
19. S.H. Li, J. Wang, X.M. Niu, Y.H. Shen, H.J. Zhang, H.-D. Sun, M.L. Li, Q.E. Tian, Y. Lu, P. Cao, and Q.T. Zheng Org. Lett. 6 2004 4327
20. H.-D. Sun, S.-X. Huang, and Q.-B. Han Nat. Prod. Rep. 23 2006 673
21. J. Gong, G. Lin, W. Sun, C.-C. Li, and Z. Yang J. Am. Chem. Soc. 132 2010 16745
22. K. Nakanishi Natural Products Chemistry 1974 Kodansha Tokyo
23. G. Vernin The Chemistry of Heterocyclic Flavoring and Aroma Compounds 1982 Ellis Horwood Chichester
24. I. Kubo, Y.W. Lee, V. Balogh-Nair, K. Nakanishi, and A. Chapya J. Chem. Soc., Chem. Commun. 1976 949
25. G. Schulte, P.J. Scheuer, and O.J. McConnell Helv. Chim. Acta 63 1980 2159
26. D. Bonne, Y. Coquerel, T. Constantieux, and J. Rodriguez Tetrahedron: Asymmetry 21 2010 1085
27. A.M. Maharramov, N.D. Sadikhova, I.G. Mammadov, and M.A. Allahverdiyev Chem. Heterocycl. Compd. 45 2009 400
28. Q. Wang, H. Hou, L. Hui, and C. Yan J. Org. Chem. 74 2009 7403
29. N.N. Karade, S.G. Shirodkar, M.N. Patil, R.A. Potrekar, and H.N. Karade Tetrahedron Lett. 44 2003 6729
30. M. Aso, A. Ojida, G. Yang, O.J. Cha, E. Osawa, and K. Kanematsu J. Org. Chem. 58 1993 3960
31. S.B. Ferreira, C.R. Kaiser, and V.F. Ferreira Org. Prep. Proced. Int. 41 2009 211
32. B.C. Ranu, L. Adak, and S. Banerjee Tetrahedron Lett. 49 2008 4613
33. R.B. Devi, M. Henrot, M.D. Paolis, and J. Maddaluno Org. Biomol. Chem. 9 2011 6509
34. S. Maiti, T.P. Paramasivan, and J.C. Menendez Tetrahedron 66 2010 9512
35. M.J. Mphahlele, and T.B. Moekwa Org. Biomol. Chem. 3 2005 2469
36. M.-Y. Wu, M.-Q. Wang, K. Li, X.-W. Feng, T. He, N. Wang, and X.-Q. Yu Tetrahedron Lett. 52 2011 679
37. Y.R. Lee, and J.C. Hwang Eur. J. Org. Chem. 2005 1568
38. Y.R. Lee, and J.Y. Suk Tetrahedron 58 2002 2359
39. Y.R. Lee, and J.Y. Suk Tetrahedron Lett. 41 2000 4795
40. Y.R. Lee Synth. Commun. 28 1998 865
41. Y.R. Lee, and J.Y. Suk Heterocycles 48 1998 875
42. Y.R. Lee, and A.T. Morehead Jr. Tetrahedron 51 1995 4909
43. L. Xia, Y.R. Lee, S.H. Kim, and W.S. Lyoo Bull. Korean Chem. Soc. 32 2011 1554
44. J. Iqbal, B. Bhatia, and N.K. Nayyar Chem. Rev. 94 1994 519
45. B. Snider Chem. Rev. 96 1996 339
46. For selected reviews on benzofuran synthesis, see: P. Cagniant, and D. Cagniant Adv. Heterocycl. Chem. 18 1975 337
47. D.M.X. Donnelly, and M.J. Meegan A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry vol. 4 1984 Pergamon Oxford 657
48. M.G. Kadieva, and E.T. Oganesyan Chem. Heterocycl. Comp. 33 1997 1245
49. T.L. Gilchrist J. Chem. Soc. Perkin Trans. 1 2001 2491
50. X.-L. Hou, Z. Yang, and H.N.C. Wong Prog. Heterocycl. Chem. 14 2002 139
51. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893
52. T. Graening, and F. Thrun A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III Vol. 3 2008 Elsevier Oxford 497
53. L. De Luca, G. Nieddu, A. Porcheddu, and G. Giacomelli Curr. Med. Chem. 16 2009 1
54. A.K. Singh, R. Chawla, A. Rai, and L.D.S. Yadav Chem. Commun. 48 2012 3766
55. A. Rai, A.K. Singh, P. Singh, and L.D.S. Yadav Tetrahedron Lett. 52 2011 1354
56. A. Rai, A.K. Singh, S. Singh, and L.D.S. Yadav Synlett 2011 335
57. S.N. Murthy, B. Madhav, V.P. Reddy, K.R. Rao, and Y.V.D. Nageswar Tetrahedron Lett. 50 2009 5009
58. N. Suryakiran, T.S. Reddy, and Y. Venkateswarlu J. Sulfur Chem. 28 2007 513