Nickel-catalyzed regio- and stereoselective reductive coupling between methylenecyclopropanes, aldehydes, and triethylborane with retention of the cyclopropane ring

Chemistry - A European Journal

Volumn 18, Issue 20, 2012, Pages 6142-6146

  Ogata, Kenichi ^a   Shimada, Daisuke ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

alkenes; cyclic compound; methylenecyclopropane; nickel; synthetic methods

Indexed keywords

CYCLIC COMPOUNDS; CYCLOPROPANE RING; METHYLENECYCLOPROPANES; REDUCTIVE COUPLING REACTION; REDUCTIVE COUPLINGS; STEREO-SELECTIVE; STEREOGENIC CARBONS; SYNTHETIC METHODS; TRIETHYLBORANE;

ALDEHYDES; NICKEL; OLEFINS; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS; STEREOSELECTIVITY;

PROPANE;

EID: 84860742102     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200271     Document Type: Article

References (50)

1. J. Montgomery, Angew. Chem. 2004, 116, 3980
2. Angew. Chem. Int. Ed. 2004, 43, 3890.
3. E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065
4. X.-Q. Tang, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 6098
5. X.-Q. Tang, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 6098
6. X.-Q. Tang, J. Montgomery, J. Am. Chem. Soc. 2000, 122, 6950
7. W.-S. Huang, J. Chan, T. F. Jamison, Org. Lett. 2000, 2, 4221
8. K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc. 2003, 125, 3442
9. G. M. Mahandru, G. Liu, J. Montgomery, J. Am. Chem. Soc. 2004, 126, 3698
10. A. Herath, J. Montgomery, J. Am. Chem. Soc. 2006, 128, 14030
11. K. Sa-Ei, J. Montgomery, Org. Lett. 2006, 8, 4441
12. M. R. Chaulagain, G. J. Sormunen, J. Montgomery, J. Am. Chem. Soc. 2007, 129, 9568
13. R. D. Baxter, J. Montgomery, J. Am. Chem. Soc. 2008, 130, 9662
14. N. Saito, T. Katayama, Y. Sato, Org. Lett. 2008, 10, 3829
15. H. A. Malik, M. R. Chaulagain, J. Montgomery, Org. Lett. 2009, 11, 5734
16. H. A. Malik, G. J. Sormunen, J. Montgomery, J. Am. Chem. Soc. 2010, 132, 6304.
17. S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 14194
18. C.-Y. Ho, T. F. Jamison, Angew. Chem. 2007, 119, 796
19. Angew. Chem. Int. Ed. 2007, 46, 782
20. Y. Yang, S.-F. Zhu, H.-F. Duan, C.-Y. Zhou, L-.X. Wang, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 2248.
21. M. Kimura, A. Ezoe, M. Mori, K. Iwata, Y. Tamaru, J. Am. Chem. Soc. 2006, 128, 8559
22. R. Sawaki, Y. Sato, M. Mori, Org. Lett. 2004, 6, 1131
23. Y. Sato, Y. Hinata, R. Seki, Y. Oonishi, N. Saito, Org. Lett. 2007, 9, 5597.
24. S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 7320.
25. K. Ogata, Y. Atsuumi, D. Shimada, S.-i. Fukuzawa, Angew. Chem. 2011, 123, 6018
26. Angew. Chem. Int. Ed. 2011, 50, 5896.
27. K. Ogata, Y. Atsuumi, S.-i. Fukuzawa, Org. Lett. 2010, 12, 4536.
28. I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 344, 111
29. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117.
30. M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 2000, 122, 11015
31. K. Kamikawa, Y. Shimizu, S. Takemoto, H. Matsuzawa, Org. Lett. 2006, 8, 4011
32. S. Komagawa, S. Saito, Angew. Chem. 2006, 118, 2506
33. Angew. Chem. Int. Ed. 2006, 45, 2446
34. S. Saito, S. Komagawa, I. Azumaya, M. Masuda, J. Org. Chem. 2007, 72, 9114
35. T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 3518
36. H. Taniguchi, T. Ohmura, M. Suginome, J. Am. Chem. Soc. 2009, 131, 11298
37. S. Komagawa, K. Takeuchi, I. Sotome, I. Azumaya, H. Masu, R. Yamasaki, S. Saito, J. Org. Chem. 2009, 74, 3323
38. R. Yamasaki, N. Terashima, I. Sotome, S. Komagawa, S. Saito, J. Org. Chem. 2010, 75, 480
39. S. Saito, K. Maeda, R. Yamasaki, T. Kitamura, M. Nakagawa, K. Kato, I. Azumaya, H. Masu, Angew. Chem. 2010, 122, 1874
40. Angew. Chem. Int. Ed. 2010, 49, 1830
41. M. Ohashi, T. Taniguchi, S. Ogoshi, Organometallics 2010, 29, 2386.
42. D. Takeuchi, K. Anada, K. Osakada, Angew. Chem. 2004, 116, 1253
43. Angew. Chem. Int. Ed. 2004, 43, 1233
44. T. Pohlmann, A. de Meijere, Org. Lett. 2000, 2, 3877
45. G.-Q. Tian, M. Shi, Org. Lett. 2007, 9, 4917
46. L.-X. Shao, M.-H. Qi, M. Shi, Tetrahedron Lett. 2008, 49, 165
47. S. I. Kozhushkov, D. S. Yufit, L. Ackermann, Org. Lett. 2008, 10, 3409
48. M. Shirakura, M. Suginome, J. Am. Chem. Soc. 2009, 131, 5060.
49. W. A. Donaldson, Tetrahedron 2001, 57, 8589.
50. In the reductive coupling reaction in the presence of triethylborane, triethylborane coordination probably accelerates the oxidative cyclization of methylenecyclopropane with aldehyde, see:, P. R. McCarren, P. Liu, P. H.-Y. Cheong, T. F. Jamison, K. N. Houk, J. Am. Chem. Soc. 2009, 131, 6654.