Formation of chiral C(sp3)-C(sp) bond by allylic substitution of secondary allylic picolinates and alkynyl copper reagents

Journal of Organic Chemistry

Volumn 74, Issue 19, 2009, Pages 7489-7495

  Kiyotsuka, Yohei ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDINES; ALKYNYLS; ALLYLIC ALCOHOL; ALLYLIC SUBSTITUTION; CHEMICAL EQUATIONS; CHIRALITY TRANSFER; PICOLINATES; PYRAZINES;

CHIRALITY; COPPER; ENANTIOMERS; ESTERIFICATION; FUNCTIONAL ELECTRIC STIMULATION; REGIOSELECTIVITY; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

ESTERS;

ALKYNYL COPPER; ALLYLIC PICOLINATE DERIVATIVE; BROMINE DERIVATIVE; COPPER; MAGNESIUM BROMIDE; PICOLINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND;

ALKYNES; ALLYL COMPOUNDS; COPPER; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PICOLINIC ACIDS; STEREOISOMERISM;

EID: 70349473079     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901728b     Document Type: Article

References (66)

1. (a) Negishi, E.; Liu, F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.;Wiley-VCH:Weinheim, 1998; Chapter 1.
2. (b) Kar, A.; Argade, N. P. Synthesis 2005, 2995-3022.
3. (a) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273-7274.
4. (b) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708.
5. (c) Spino, C.; Beaulieu, C. J. Am. Chem. Soc. 1998, 120, 11832-11833.
6. (d) Belelie, J. L.; Chong, J. M. J. Org. Chem. 2002, 67, 3000-3006.
7. (e) Perrone, S.; Knochel, P. Org. Lett. 2007, 9, 1041-1044.
8. (a)Kiyotsuka, Y.; Acharya, H. P.;Katayama, Y.;Hyodo, T.;Kobayashi, Y. Org. Lett. 2008, 10, 1719-1722.
9. (b) Kiyotsuka, Y.;Kobayashi, Y. Tetrahedron Lett. 2008, 49, 7256-7259.
10. (c) Kiyotsuka, Y.; Katayama, Y.; Acharya, H. P.; Hyodo, T.; Kobayashi, Y. J. Org. Chem. 2009, 74, 1939-1951.
11. (a) Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1972, 94, 7210-7211.
12. (b) House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893-3901.
13. (c) Corey, E. J.; Floyd, D.; Lipshutz, B. H. J. Org. Chem. 1978, 43, 3418-3420.
14. (a) Wu, T. R.; Chong, J.M. J. Am. Chem. Soc. 2005, 127, 3244-3245.
15. (b) Knöpfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 9682-9683.
16. (c) Pellegrinet, S. C.; Goodman, J. M. J. Am. Chem. Soc. 2006, 128, 3116-3117.
17. Matveeva, E. D.; Yerin, A. S.; Kurts, A. L. Russ. J. Org. Chem. 2000, 36, 15721576;
18. Zh. Org. Khim. 2000, 36, 1619-1623.
19. (a) Jeffery, T. Tetrahedron Lett. 1989, 30, 2225-2228.
20. (b) Mignani, G.; Chevalier, C.; Grass, F.; Allmang, G.; Morel, D. Tetrahedron Lett. 1990, 31, 5161-5164. and references therein.
21. 3)-C(sp) bond by using substitution at propargylic carbon: (a) Inada, Y.; Nishibayashi, Y.; Uemura, S. Angew. Chem., Int. Ed. 2005, 44, 7715-7717.
22. (b) Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 12645-12647.
23. (c) Smith, S. W.; Fu, G. C. Idem Angew. Chem., Int. Ed. 2008, 47, 9334-9336.
24. (d) Rubenbauer, P.; Herdtweck, E.; Strassner, T.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 10106-10109.
25. 3)-C(sp) bonds: (a) Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410-5411.
26. (b) Shirakura, M.; Suginome, M. Idem Org. Lett. 2009, 11, 523-526.
27. (c) Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510-13511.
28. Yadav, J. S.; Deshpande, P. K.; Sharma, G. V. M. Tetrahedron 1990, 46, 7033-7046.
29. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
30. Attempted Lindlar reduction of the phosphate of rac-12 produced deoxygenated compound, while the carbonate and the acetate of rac-12 produced saturated compounds.
31. Phosphates: (a) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130-1136.
32. (b) Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. J. Org. Chem. 1997, 62, 6344-6352.
33. (c) Calaza, M. I.; Hupe, E.; Knochel, P. Org. Lett. 2003, 5, 1059-1061.
34. (d) Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
35. (e) Soorukram, D.; Knochel, P. Org. Lett. 2004, 6, 2409-2411.
36. (f) L. Belelie, J.; Chong, J. M. J. Org. Chem. 2001, 66, 5552-5555.
37. (g) Whitehead, A.; McParland, J. P.; Hanson, P. R. Org. Lett. 2006, 8, 5025-5028.
38. (h) Niida, A.; Tanigaki, H.; Inokuchi, E.; Sasaki, Y.; Oishi, S.; Ohno, H.; Tamamura, H.; Wang, Z.; Peiper, S. C.; Kitaura, K.; Otaka, A.; Fujii, N. J. Org. Chem. 2006, 71, 3942-3951.
39. Pentafluorobenzoates: (a) Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111-2114.
40. (b) Calaza, M. I.; Yang, X.; Soorukram, D.; Knochel, P. Org. Lett. 2004, 6, 529-531.
41. (c) Leuser, H.; Perrone, S.; Liron, F.; Kneisel, F. F.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 4627-4631.
42. (d) Soorukram, D.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3686-3689.
43. (e) Soorukram, D.; Knochel, P. Org. Lett. 2007, 9, 1021-1023.
44. (f) See ref 2e.
45. o-Diphenylphosphinobenzoates: (a) Breit, B.; Demel, P. Adv. Synth. Catal. 2001, 343, 429-432.
46. (b) Demel, P.; Keller, M.; Breit, B. Chem.-Eur. J. 2006, 12, 6669-6683.
47. (c) Breit, B.; Herber, C. Angew. Chem., Int. Ed. 2004, 43, 3790-3792.
48. (d) Herber, C.; Breit, B. Chem.-Eur. J. 2006, 12, 6684-6691.
49. (e) Herber, C.; Breit, B. Angew. Chem., Int. Ed. 2005, 44, 5267-5269.
50. Nieto, S.; Metola, P.; Lynch, V. M.; Anslyn, E. V. Organometallics 2008, 27, 3608-3610.
51. For example: (a) Breit, B.; Demel, P.; Studte, C. Angew. Chem., Int. Ed. 2004, 43, 3786-3789.
52. (b) Breit, B.; Demel, P.; Grauer, D.; Studte, C. Chem. Asian J. 2006, 1, 586-597. See also refs 2a, 3, and 14a.
53. 2S afforded alcohol 30.
54. olefinic-H=15 Hz).
55. CT, defined as (% ee of product/% ee of substrate) × 100, was determined by chiral HPLC.
56. D values were compared to determine their absolute configurations. See the Experimental Section for the former and the Supporting Information for the latter. Other products were assigned by analogy.
57. 2OPMB, 5.5-5.6 (m) for CH=CH).
58. Prepared by the following method: (Chemical Equation Presented)
59. N2′ product v in moderate yield.
60. 4NF gave a mixture of products.
61. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
62. Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046-16047.
63. A similar reaction of rac-42 with azide 50 in aqueous t-BuOH gave amide vi in 47% yield.
64. olefinic-H=11 Hz) was determined. See Supporting Information.
65. Yadav, J. S.; Nanda, S. Tetrahedron: Asymmetry 2001, 12, 3223-3234.
66. Hydrogenation of (S)-42 with 10% Pd/C in EtOAc resulted in partial racemization.