Enantioselective synthesis of highly functionalized dihydrofurans through copper-catalyzed asymmetric formal [3+2] cycloaddition of β-ketoesters with propargylic esters

Angewandte Chemie - International Edition

Volumn 53, Issue 38, 2014, Pages 10223-10227

  Zhu, Fu Lin ^a,b   Wang, Ya Hui ^a   Zhang, De Yang ^a,b   Xu, Jie ^a   Hu, Xiang Ping ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

2,3 dihydrofurans; asymmetric catalysis; copper; cycloadditions; synthetic methods

Indexed keywords

CATALYSIS; CHEMICAL BONDS; CYCLOADDITION; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; STEREOCHEMISTRY;

2 ,3-DIHYDROFURANS; ASYMMETRIC CATALYSIS; ASYMMETRIC [3+2] CYCLOADDITION; CYCLOADDITIONS; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; SYNTHETIC METHODS; [3+2]-CYCLOADDITION;

COPPER;

2,3-DIHYDROFURAN; COPPER; ESTER; FURAN DERIVATIVE; ORGANOMETALLIC COMPOUND;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ESTERS; FURANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84908064850     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405857     Document Type: Article

References (77)

1. B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819
2. B. M. Fraga, Nat. Prod. Rep. 1992, 9, 217-241
3. A. T. Merritt, S. B. Ley, Nat. Prod. Rep. 1992, 9, 243-287
4. M. M. Faul, B. E. Huff, Chem. Rev. 2000, 100, 2407-2474
5. M. C. Elliott, J. Chem. Soc. Perkin Trans. 1 2002, 2301-2323
6. F. Garzino, A. Méou, P. Brun, Synthesis 2003, 598-602
7. X.-L. Hou, Z. Yang, K.-S. Yeung, H. N. C. Wong, Prog. Heterocycl. Chem. 2005, 17, 142-171
8. T. G. Kilroy, T. P. O'Sullivan, P. J. Guiry, Eur. J. Org. Chem. 2005, 4929-4949
9. J. D. Pettigrew, P. D. Wilson, Org. Lett. 2006, 8, 1427-1429.
10. M. Aso, A. Ojida, G. Yang, O. J. Cha, E. Osawa, K. Kanematsu, J. Org. Chem. 1993, 58, 3960-3968
11. F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, K. D. Treiber, J. Org. Chem. 1993, 58, 6952-6953
12. S. C. Roy, P. K. Mandal, Tetrahedron 1996, 52, 2193-2198
13. M. Hamaguchi, H. Matsubara, T. Nagai, Tetrahedron Lett. 2000, 41, 1457-1460
14. G. Bar, A. F. Parsons, C. B. Thomas, Tetrahedron Lett. 2000, 41, 7751-7755
15. F. Garzino, A. Méou, P. Brun, Tetrahedron Lett. 2000, 41, 9803-9807
16. R. Antonioletti, G. Righi, L. Oliveri, P. Bovicelli, Tetrahedron Lett. 2000, 41, 10127-10130
17. Y. R. Lee, B. S. Kim, D. H. Kim, Tetrahedron 2000, 56, 8845-8853
18. Y. Wang, S. Zhu, Tetrahedron 2001, 57, 3383-3387
19. V. K. Yadav, R. Balamurugan, Org. Lett. 2001, 3, 2717-2719
20. Y. Zhang, A. J. Raines, R. A. Flowers II, Org. Lett. 2003, 5, 2363-2365
21. V. Calò, F. Scordari, A. Nacci, E. Schingaro, L. D'Accolti, A. Monopoli, J. Org. Chem. 2003, 68, 4406-4409
22. F. Garzino, A. Méou, P. Brun, Eur. J. Org. Chem. 2003, 1410-1414
23. C. Xing, S. Zhu, J. Org. Chem. 2004, 69, 6486-6488
24. H. J. Gais, L. R. Reddy, G. S. Babu, G. Raabe, J. Am. Chem. Soc. 2004, 126, 4859-4864
25. R. Caliskan, T. Pekel, W. H. Watson, M. Balci, Tetrahedron Lett. 2005, 46, 6227-6230
26. W. Xia, C. Yang, B. O. Patrick, J. R. Scheffer, C. Scott, J. Am. Chem. Soc. 2005, 127, 2725-2730
27. A. M. Bernard, A. Frongia, P. P. Piras, F. Secci, M. Spiga, Org. Lett. 2005, 7, 4565-4568
28. R. K. Bowman, J. S. Jonhson, Org. Lett. 2006, 8, 573-576
29. J.-C. Zheng, C.-Y. Zhu, X.-L. Sun, Y. Tang, L.-X. Dai, J. Org. Chem. 2008, 73, 6909-6912
30. R. Zhang, Y. Liang, G. Zhou, K. Wang, D. Dong, J. Org. Chem. 2008, 73, 8089-8092
31. Z. Chen, J. Zhang, Chem. Asian J. 2010, 5, 1542-1545
32. M. Li, S. Lin, Z. Dong, X. Zhang, F. Liang, J. Zhang, Org. Lett. 2013, 15, 3978-3981
33. L. Xia, Y. R. Lee, Adv. Synth. Catal. 2013, 355, 2361-2374.
34. H. M. L. Davies, G. Ahmed, R. L. Calvo, M. R. Churchill, J. Org. Chem. 1998, 63, 2641-2645
35. P. Müller, G. Bernardinelli, Y. F. Allenbach, M. Ferri, S. Grass, Synlett 2005, 1397-1400
36. S. Son, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 1046-1047
37. J.-L. Zhou, L.-J. Wang, H. Xu, X.-L. Sun, Y. Tang, ACS Catal. 2013, 3, 685-688. For organocatalytic Feist-Bènary reactions to form chiral 2,3-dihydrofurans, see
38. M. A. Calter, R. M. Phillips, C. Flaschenriem, J. Am. Chem. Soc. 2005, 127, 14566-14567
39. M. Rueping, A. Parra, U. Uria, F. Besselièvre, E. Merino, Org. Lett. 2010, 12, 5680-5683
40. L.-P. Fan, P. Li, X.-S. Li, D.-C. Xu, M.-M. Ge, W.-D. Zhu, J.-W. Xie, J. Org. Chem. 2010, 75, 8716-8719
41. X. Dou, F. Zhong, Y. Lu, Chem. Eur. J. 2012, 18, 13945-13948; For other methods, see
42. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, Organometallics 1993, 12, 4188-4196
43. D. A. Evans, Z. K. Sweeney, T. Rovis, J. S. Tedrow, J. Am. Chem. Soc. 2001, 123, 12095-12096.
44. V. Cadierno, J. Gimeno, N. Nebra, Adv. Synth. Catal. 2007, 349, 382-394
45. R. Sanz, D. Miguel, A. Martínez, J. M. Álvarez-Gutiérrez, F. Rodríguez, Org. Lett. 2007, 9, 727-730
46. X. Feng, Z. Tan, D. Chen, Y. Shen, C.-C. Guo, J. Xiang, C. Zhu, Tetrahedron Lett. 2008, 49, 4110-4112
47. W. Ji, Y. Pan, S. Zhao, Z. Zhan, Synlett 2008, 3046-3052
48. Y. Pan, S. Zhao, W. Jin, Z. Zhan, J. Comb. Chem. 2009, 11, 103-109
49. G. Aridoss, K. K. Laali, Tetrahedron Lett. 2011, 52, 6859-6864.
50. Y.-F. Chen, H.-F. Wang, Y. Wang, Y.-C. Luo, H.-L. Zhu, P.-F. Xu, Adv. Synth. Catal. 2010, 352, 1163-1168
51. X. Meng, S. Kim, Synlett 2012, 1960-1964.
52. N. Ljungdahl, N. Kann, Angew. Chem. 2009, 121, 652-654
53. Angew. Chem. Int. Ed. 2009, 48, 642-644
54. Y. Miyake, S. Uemura, Y. Nishibayashi, ChemCatChem 2009, 1, 342-356
55. R. J. Detz, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2009, 6263-6276
56. C.-H. Ding, X.-L. Hou, Chem. Rev. 2011, 111, 1914-1937
57. Y. Nishibayashi, Synthesis 2012, 489-503
58. E. B. Bauer, Synthesis 2012, 1131-1151; For selected examples, see
59. R. J. Detz, M. M. E. Delville, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2008, 120, 3837-3840
60. Angew. Chem. Int. Ed. 2008, 47, 3777-3780
61. G. Hattori, H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2008, 120, 3841-3843
62. Angew. Chem. Int. Ed. 2008, 47, 3781-3783
63. G. Hattori, A. Yoshida, Y. Miyake, Y. Nishibayashi, J. Org. Chem. 2009, 74, 7603-7607
64. P. Fang, X.-L. Hou, Org. Lett. 2009, 11, 4612-4615
65. G. Hattori, Y. Miyake, Y. Nishibayashi, ChemCatChem 2010, 2, 155-158
66. G. Hattori, K. Sakata, H. Matsuzawa, Y. Tanabe, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2010, 132, 10592-10608
67. R. J. Detz, Z. Abiri, R. le Griel, H. Hiemstra, J. H. van Maarseveen, Chem. Eur. J. 2011, 17, 5921-5930
68. A. Yoshida, G. Hattori, Y. Miyake, Y. Nishibayashi, Org. Lett. 2011, 13, 2460-2463
69. A. Yoshida, M. Ikeda, G. Hattori, Y. Miyake, Y. Nishibayashi, Org. Lett. 2011, 13, 592-595
70. C. Zhang, X.-H. Hu, Y.-H. Wang, Z. Zheng, J. Xu, X.-P. Hu, J. Am. Chem. Soc. 2012, 134, 9585-9588
71. C. Zhang, Y.-H. Wang, X.-H. Hu, Z. Zheng, J. Xu, X.-P. Hu, Adv. Synth. Catal. 2012, 354, 2854-2858
72. T. Mino, H. Taguchi, M. Hashimoto, M. Sakamoto, Tetrahedron: Asymmetry 2013, 24, 1520-1523
73. F.-Z. Han, F.-L. Zhu, Y.-H. Wang, Y. Zou, X.-H. Hu, S. Chen, X.-P. Hu, Org. Lett. 2014, 16, 588-591
74. Y. Zhou, F.-L. Zhu, Z.-C. Duan, Y.-H. Wang, D.-Y. Zhang, Z. Cao, Z. Zheng, X.-P. Hu, Tetrahedron Lett. 2014, 55, 2033-2036
75. F.-L. Zhu, Y. Zou, D.-Y. Zhang, Y.-H. Wang, X.-H. Hu, S. Chen, J. Xu, X.-P. Hu, Angew. Chem. 2014, 126, 1434-1438
76. Angew. Chem. Int. Ed. 2014, 53, 1410-1414.
77. CCDC 1004895 ((R)- 3 ea) and CCDC 1004897 ((R,R)- 6 ea) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.