Regioselective and stereoselective copper(I)-Promoted allylation and conjugate addition of N -Boc-2-lithiopyrrolidine and N -Boc-2-lithiopiperidine

Journal of Organic Chemistry

Volumn 75, Issue 12, 2010, Pages 4069-4077

  Coldham, Iain ^a   Leonori, Daniele ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATIONS; CHIRAL LIGAND; CONJUGATE ADDITION; COPPER CYANIDE; COPPER IODIDE; COPPER SALT; DYNAMIC RESOLUTION; ENANTIOPURITY; FORMAL SYNTHESIS; LITHIUM CHLORIDE; PYRROLIDINES; REGIO-SELECTIVE; REGIOISOMERS; STEREO-SELECTIVE; TRANSMETALATION; UNSATURATED ESTERS; ZINC CHLORIDE;

CHLORINE COMPOUNDS; CYANIDES; ENANTIOSELECTIVITY; ESTERS; LITHIUM; SALTS; ZINC;

COPPER;

2 BUTYL 5 PROPYLPYRROLIDINE; CONICEINE; CONIINE; CUPROUS ION; LASUBINE II; N TERT BUTOXYCARBONYL 2 LITHIOPIPERIDINE; N TERT BUTOXYCARBONYL 2 LITHIOPYRROLIDINE; NORHYGRINE; PELLETIERINE; PIPERIDINE DERIVATIVE; PSEUDOHYGROLINE; PYRROLIDINE DERIVATIVE; SEDRIDINE; UNCLASSIFIED DRUG; ZINC; ZINC CHLORIDE;

ADDITION REACTION; ALLYLATION; ARTICLE; ENANTIOSELECTIVITY; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 77953502791     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100415x     Document Type: Article

References (73)

1. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
2. Rappoport, Z.; Marek, I. The Chemistry of Organolithium Compounds; Wiley: Chichester, 2004.
3. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117
4. Uchiyama, M.; Nakamura, S.; Furuyama, T.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2007, 129, 13360
5. Klein, S.; Marek, I.; Normant, J.-F. J. Org. Chem. 1994, 59, 2925
6. Yus, M.; Ortiz, R. Eur. J. Org. Chem. 2004, 3833
7. Erdik, E. Tetrahedron 1984, 40, 641
8. Kocienski, P.; Wadman, S.; Cooper, K. J. Am. Chem. Soc. 1989, 111, 2363
9. Breit, B.; Schmidt, Y. Chem. Rev. 2008, 108, 2928
10. Ortiz, R.; Yus, M. Tetrahedron 2005, 61, 1699
11. Haubrich, A.; van Klaveren, M.; van Koten, G.; Handke, G.; Krause, N. J. Org. Chem. 1993, 58, 5849
12. Pastor, I. M.; Yus, M. Tetrahedron 2001, 57, 2371
13. Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
14. The Chemistry of Organocopper Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2009.
15. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109
16. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine: Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and Its Derivatives; Elsevier: Amsterdam, 1991.
17. OHagan, D. Nat. Prod. Rep. 2000, 435
18. Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693
19. Dieter, R. K.; Lu, K. J. Org. Chem. 2002, 67, 847
20. Li, S. J.; Dieter, R. K. J. Org. Chem. 2003, 68, 969
21. Dieter, R. K.; Chen, N.; Yu, H.; Nice, L. E.; Gore, V. K. J. Org. Chem. 2005, 70, 2109
22. Dieter, R. K.; Sharma, R. R. Tetrahedron Lett. 1997, 38, 5937
23. Dieter, R. K.; Topping, C. M.; Nice, L. E. J. Org. Chem. 2001, 66, 2302
24. Dieter, R. K.; Lu, K.; Velu, S. E. J. Org. Chem. 2000, 65, 8715
25. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231
26. Dieter, R. K.; Oba, G.; Chandupatla, C.; Topping, C. M.; Lu, K.; Watson, R. T. J. Org. Chem. 2004, 69, 3076
27. Coldham, I.; Patel, J. J.; Raimbault, S.; Whittaker, D. T. E. Chem. Commun. 2007, 4534
28. Coldham, I.; OBrien, P.; Patel, J. J.; Raimbault, S.; Sanderson, A. J.; Stead, D.; Whittaker, D. T. E. Tetrahedron: Asymmetry 2007, 18, 2113
29. Coldham, I.; Raimbault, S.; Chovatia, P. T.; Patel, J. J.; Leonori, D.; Sheikh, N. S.; Whittaker, D. T. E. Chem. Commun. 2008, 4174
30. Coldham, I.; Leonori, D. Org. Lett. 2008, 10, 3923
31. Dieter, R. K.; Velu, S. E.; Nice, L. E. Synlett 1997, 1114
32. Dieter, R. K.; Gore, V. K.; Chen, N. Org. Lett. 2004, 6, 763
33. Stead, D.; OBrien, P.; Sanderson, A. J. Org. Lett. 2005, 7, 4459
34. Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2002, 4, 119
35. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390
36. Yus, M.; Gomis, J. Eur. J. Org. Chem. 2003, 2043
37. Dieter, R. K.; Watson, R. T.; Goswami, R. Org. Lett. 2004, 6, 253
38. Goering, H. L.; Seitz, E. P.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304
39. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063
40. Yoshikai, N.; Zhang, S.-L.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 12862
41. Streitwieser, A.; Jayasree, E. G.; Hasanayn, F.; Leung, S. S.-H. J. Org. Chem. 2008, 73, 9426
42. Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 5560
43. Sakata, H.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 5719
44. Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349
45. Yamamoto, Y. Angew. Chem., Int. Ed. 1986, 25, 947
46. Ibuka, T.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Am. Chem. Soc. 1989, 111, 4864
47. Taylor, R. J. K. Organocopper Reagents: A Practical Approach; Oxford University Press: Oxford, 1994.
48. Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1991, 56, 5491
49. Bartholmew, E. R.; Bertz, S. H.; Cope, S.; Murphy, M.; Ogle, C. A. J. Am. Chem. Soc. 2008, 130, 11244
50. Bailey, W. F.; Beak, P.; Kerrick, S. T.; Ma, S.; Wiberg, K. B. J. Am. Chem. Soc. 2002, 124, 1889
51. McGrath, M. J.; Bilke, J. L.; OBrien, P. Chem. Commun. 2006, 2607
52. Coldham, I.; Raimbault, S.; Whittaker, D. T. E.; Chovatia, P. T.; Leonori, D.; Patel, J. J.; Sheikh, N. S. Chem. Eur. J. 2010, 16, 4082.
53. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry 1998, 9, 1951
54. Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Smith, A. D. Tetrahedron 2009, 65, 10192
55. Pomilio, A. B.; Gonzalez, M. D.; Eceizabarrena, C. C. Phytochemistry 1996, 41, 1393
56. Baxter, G.; Melville, J. C.; Robins, D. J. Synlett 1991, 359
57. Cuny, G. D.; Buchwald, S. L. Synlett 1995, 519
58. Hjelmgaard, T.; Gardette, D.; Tanner, D.; Aitken, D. J. Tetrahedron: Asymmetry 2007, 18, 671
59. Dieter, R. K.; Chen, N.; Watson, R. T. Tetrahedron 2005, 61, 3221
60. Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047
61. Ringdahl, B.; Pinder, A. R.; Pereira, W. E.; Oppenheimer, N. J.; Craig, J. C. J. Chem. Soc., Perkin Trans. 1 1984, 1
62. Jones, T. H.; Voegtle, H. L.; Miras, H. M.; Weatherford, R. G.; Spande, T. F.; Garraffo, H. M.; Daly, J. W.; Davidson, D. W.; Snelling, R. R. J. Nat. Prod. 2007, 70, 160
63. Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826
64. Hande, S. M.; Kawai, N.; Uenishi, J. J. Org. Chem. 2009, 74, 244
65. Lauzon, S.; Tremblay, F.; Gagnon, D.; Godbout, C.; Chabot, C.; Mercier-Shanks, C.; Perreault, S.; DeSeve, H.; Spino, C. J. Org. Chem. 2008, 73, 6239
66. Castro, A.; Ramirez, J.; Juarez, J.; Teran, J. L.; Orea, L.; Galindo, A.; Gnecco, D. Heterocycles 2007, 71, 2699
67. Etxebarria, J.; Vicario, J. L.; Badia, D.; Carrillo, L. Tetrahedron 2007, 63, 11421
68. Fustero, S.; Jimenez, D.; Moscardo, J.; Catalan, S.; del Pozo, C. Org. Lett. 2007, 9, 5283
69. Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Org. Lett. 2007, 9, 2473
70. Cheng, G.; Wang, X.; Su, D.; Liu, H.; Liu, F.; Hu, Y. J. Org. Chem. 2010, 75, 1911-1916
71. Carlson, E. C.; Rathbone, L. K.; Yang, H.; Collett, N. D.; Carter, R. G. J. Org. Chem. 2008, 73, 5155
72. Blarer, D. J.; Seebach, D. Chem. Ber. 1983, 116, 2250
73. Passarella, D.; Barilli, A.; Belinghieri, F.; Fassi, P.; Riva, S.; Sacchetti, A.; Silvani, A.; Danieli, B. Tetrahedron: Asymmetry 2005, 16, 2225