Enantioselective conversion of primary alcohols to α- Exo -methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(Alkoxycarbonyl)allylation

Journal of the American Chemical Society

Volumn 134, Issue 27, 2012, Pages 11100-11103

  Montgomery, T Patrick ^a   Hassan, Abbas ^a   Park, Boyoung Y ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ESTER; BOND FORMING; BUTYROLACTONES; C-C COUPLING; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE; IRIDIUM CATALYST; PRIMARY ALCOHOLS; TRANSFER HYDROGENATIONS;

ALDEHYDES; ORGANIC COMPOUNDS;

IRIDIUM;

ALCOHOL DERIVATIVE; ALDEHYDE; CARBON; ESTER DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; IRIDIUM;

ALLYLATION; ARTICLE; BROMINATION; CATALYSIS; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; HYDROGENATION; STEREOCHEMISTRY;

4-BUTYROLACTONE; ALCOHOLS; ALLYL COMPOUNDS; CATALYSIS; HYDROGENATION; IRIDIUM; STEREOISOMERISM;

EID: 84863848207     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303839h     Document Type: Article

References (64)

1. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94
2. Kuroda, C.; Suzuki, H. Curr. Org. Chem. 2003, 7, 115
3. Konaklieva, M. I.; Plotkin, B. J. Mini-Rev. Med. Chem. 2005, 5, 73
4. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
5. Elford, T. G.; Hall, D. G. Synthesis 2010, 893
6. Albrecht, A.; Albrecht, L.; Janecki, T. Eur. J. Org. Chem. 2011, 2747
7. Chataigner, I.; Lebreton, J.; Zammattio, F.; Villiéras, J. Tetrahedron Lett. 1997, 38, 3719
8. Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898
9. Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586
10. Kennedy, J. W. J.; Hall, D. G. J. Org. Chem. 2004, 69, 4412
11. Ramachandran, P. V.; Pratihar, D.; Biswas, D.; Srivastava, A.; Reddy, M. V. R. Org. Lett. 2004, 6, 481
12. Yu, S. H.; Ferguson, M. J.; McDonald, R.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 12808
13. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325
14. Kabalka, G. W.; Venkataiah, B.; Chen, C. Tetrahedron Lett. 2006, 47, 4187
15. Ramachandran, P. V.; Pratihar, D.; Biswas, D. Org. Lett. 2006, 8, 3877
16. Elford, T. G.; Arimura, Y.; Yu, S. H.; Hall, D. G. J. Org. Chem. 2007, 72, 1276
17. Ramachandran, P. V.; Pratihar, D. Org. Lett. 2007, 9, 2087
18. Mitra, S.; Gurrala, S. R.; Coleman, R. S. J. Org. Chem. 2007, 72, 8724
19. Chataigner, I.; Zammattio, F.; Lebreton, J.; Villiéras, J. Tetrahedron Lett. 2008, 64, 2441
20. Hosomi, A.; Hashimoto, H.; Sakurai, H. Tetrahedron Lett. 1980, 21, 951
21. Nishitani, K.; Yamakawa, K. Tetrahedron Lett. 1987, 28, 655
22. Kuroda, C.; Shimizu, S.; Satoh, J. Y. J. Chem. Soc., Chem. Commun. 1987, 286
23. Kuroda, C.; Shimizu, S.; Satoh, J. Y. J. Chem. Soc., Perkin Trans. 1 1990, 519
24. Nishitani, K.; Yamakawa, K. Tetrahedron Lett. 1991, 32, 387
25. Nishitani, K.; Nakamura, Y.; Orii, R.; Arai, C.; Yamakawa, K. Chem. Pharm. Bull. 1993, 41, 822
26. Kuroda, C.; Shimizu, S.; Haishima, T.; Satoh, J. Y. Bull. Chem. Soc. Jpn. 1993, 66, 2298
27. Kuroda, C.; Ito, K. Bull. Chem. Soc. Jpn. 1996, 69, 2297
28. Tanaka, K.; Yoda, H.; Isobe, Y.; Kaji, A. Tetrahedron Lett. 1985, 26, 1337
29. Tanaka, K.; Yoda, H.; Isobe, Y.; Kaji, A. J. Org. Chem. 1986, 51, 1856
30. Baldwin, J. E.; Adlington, R. M.; Sweeney, J. B. Tetrahedron Lett. 1986, 27, 5423
31. Suzuki, T.; Sengoku, T.; Takahashi, M.; Yoda, H. Tetrahedron Lett. 2008, 49, 4701
32. Suzuki, T.; Atsumi, J.-i.; Sengoku, T.; Takahashi, M.; Yoda, H. J. Organomet. Chem. 2010, 695, 128
33. Lambert, F.; Kirschleger, B.; Villiéras, J. J. Organomet. Chem. 1991, 406, 71
34. Hegedus, L. S.; Wagner, S. D.; Waterman, E. L.; Siirala-Hansen, K. J. Org. Chem. 1975, 40, 593
35. Löffler, A.; Pratt, R. J.; Rüesch, H. P.; Dreiding, A. S. Helv. Chem. Acta 1970, 53, 383
36. Öhler, E.; Reininger, K.; Schmidt, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 457
37. Okuda, Y.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Chem. Lett. 1985, 481
38. Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697
39. Nokami, J.; Tamaoka, T.; Ogawa, H.; Wakabayashi, S. Chem. Lett. 1986, 541
40. Uneyama, K.; Ueda, K.; Torii, S. Chem. Lett. 1986, 1201
41. Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225
42. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533
43. Bryan, V. J.; Chan, T.-H. Tetrahedron Lett. 1996, 37, 5341
44. Csuk, R.; Schröder, C.; Hutter, S.; Mohr, K. Tetrahedron: Asymmetry 1997, 8, 1411
45. Choudhury, P. K.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1998, 39, 3581
46. Choudhury, P. K.; Foubelo, F.; Yus, M. Tetrahedron 1999, 55, 10779
47. Lee, A. S.-Y.; Chang, Y.-T.; Wang, S.-H.; Chu, S.-F. Tetrahedron Lett. 2002, 43, 8489
48. Paira, M.; Banerjee, B.; Jana, S.; Mandel, S. K.; Roy, S. C. Tetrahedron Lett. 2007, 48, 3205
49. Bower, J. F.; Krische, M. J. Top. Organomet. Chem. 2011, 43, 107
50. Hassan, A.; Krische, M. J. Org. Process Res. Dev. 2011, 15, 1236
51. Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340
52. Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891
53. Cramer, R. J. Am. Chem. Soc. 1967, 89, 4621
54. Jesse, A. C.; Cordfunke, E. H. P.; Ouweltjes, W. Thermochim. Acta 1979, 30, 293
55. Dewar, M. J. S. Bull. Soc. Chim. Fr. 1951, C71
56. Chatt, J.; Duncanson, L. A. J. Chem. Soc. 1953, 2939
57. Dewar, M. J. S.; Ford, G. P. J. Am. Chem. Soc. 1979, 101, 783
58. Stahl, S. S.; Thorman, J. L.; de Silva, N.; Guzei, I. A.; Clark, R. W. J. Am. Chem. Soc. 2003, 125, 12
59. Popp, B. V.; Thorman, J. L.; Morales, C. M.; Landis, C. R.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 14832
60. Hassan, A.; Zbieg, J. R.; Krische, M. J. Angew. Chem., Int. Ed. 2011, 50, 3493
61. Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicoló, F. J. Org. Chem. 2000, 65, 2043
62. Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405
63. Ando, M.; Wada, T.; Isogai, K. J. Org. Chem. 1991, 56, 6235
64. Hodgson, D. M.; Talbot, E. P. A.; Clark, B. P. Org. Lett. 2011, 13, 2594