Palladium-catalyzed asymmetric formal [3+2] cycloaddition of vinyl cyclopropanes and β,γ-unsaturated α-keto esters: An effective route to highly functionalized cyclopentanes

Organometallics

Volumn 31, Issue 21, 2012, Pages 7591-7599

  Mei, Liang Yong ^a   Wei, Yin ^b   Xu, Qin ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO- AND ENANTIOSELECTIVITY; HIGHLY FUNCTIONALIZED CYCLOPENTANES; KETO ESTER; PALLADIUM-CATALYZED;

CATALYSIS; ESTERIFICATION; ESTERS; PHOSPHORUS COMPOUNDS;

PROPANE;

EID: 84869054111     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300896z     Document Type: Article

References (42)

1. Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 2000, 1, 477-501
2. Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72
3. Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C. Chem. Rev. 1989, 89, 165-198
4. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
5. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347
6. Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31
7. Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632
8. Paquette, L. A. Chem. Rev. 1986, 86, 733-750
9. Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135
10. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117-3179
11. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92
12. Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467-1486
13. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316
14. Helmchen, G.; Ernst, M.; Paradies, G. Pure Appl. Chem. 2004, 76, 495-506
15. Little, R. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; pp 239-270.
16. Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229-267
17. Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247-335
18. Burgess, K. J. Org. Chem. 1987, 52, 2046-2051
19. Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871-2874
20. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1985, 26, 3825-3828
21. Hiroi, K.; Yamada, A. Tetrahedron: Asymmetry 2000, 11, 1835-1841
22. Trost, B. M.; Morris, P. J. Angew. Chem., Int. Ed. 2011, 50, 6167-6170
23. Dieskau, A. P.; Holzwarth, M. S.; Plietker, B. J. Am. Chem. Soc. 2012, 134, 5048-5051
24. Shimizu, I.; Ohashi, Y.; Tsuji, J. Chem. Lett. 1987, 6, 1157-1158
25. Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837
26. Larksarp, C.; Alper, H. J. Org. Chem. 1998, 63, 6229-6233
27. Parsons, A. T.; Campbell, M. J.; Johnson, J. S. Org. Lett. 2008, 10, 2541-2544
28. For chiral Lewis acid catalyzed [3+2] cycloaddition of cyclopropanes with aldehydes and imines, see: Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 3122-3123
29. See also: Parsons, A. T.; Smith, A. G.; Neel, A. J.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132, 9688-9692
30. Goldberg, A. F. G.; Stoltz, B. M. Org. Lett. 2011, 13, 4474-4476
31. Mei, L.-Y.; Yuan, Z.-L.; Shi, M. Organometallics 2011, 30, 6466-6475
32. Yuan, Z.-L.; Mei, L.-Y.; Wei, Y.; Shi, M.; Kattamuri, P. V.; McDowell, P.; Li, G.-G. Org. Biomol. Chem. 2012, 10, 2509-2513
33. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779-1787
34. Deng, H.-P.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2009, 351, 2897-2902
35. Flack, H. D. Acta Crystallogr. A 1983, 39, 876-881
36. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 41, 96-103
37. Meng, Q.-H.; Zhu, L.-F.; Zhang, Z.-G. J. Org. Chem. 2008, 73, 7209-7212
38. Palacios, F.; Vicario, J.; Aparicio, D. Eur. J. Org. Chem. 2006, 2843-2850
39. Larios, E. S.; Thai, K.; Bilodeau, F.; Gravel, M. Org. Lett. 2011, 13, 4942-4945
40. Srivastava, B. K.; Joharapurkar, A.; Raval, S.; Patel, J. Z.; Soni, R.; Raval, P.; Gite, A.; Goswami, A.; Sadhwani, N.; Gandhi, N.; Patel, H.; Mishra, B.; Solanki, M.; Pandey, B.; Jain, M. R.; Patel, P. R. J. Med. Chem. 2007, 50, 5951-5966
41. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714-2720
42. Duan, H.-F.; Xie, J.-H.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2008, 47, 4351-4353