Anti-Aminoallylation of Aldehydes via ruthenium-catalyzed transfer hydrogenative coupling of sulfonamido Allenes: 1,2-Aminoalcohols

Journal of the American Chemical Society

Volumn 131, Issue 14, 2009, Pages 5054-5055

  Skucas, Eduardas ^a   Zbieg, Jason R ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PROPANOL; [CARBONYL; ALIPHATIC ALDEHYDES; ALLENES; AMINO ALCOHOLS; AROMATIC ALDEHYDE; CARBONYL ADDITION; DIASTEREO-SELECTIVITY; HYDROMETALATION; REDUCTANT; REDUCTIVE COUPLINGS; TRANSFER HYDROGENATIONS; UNSATURATED ALDEHYDES;

AMINES; CARBONYLATION; DEUTERIUM; RUTHENIUM;

ALDEHYDES;

ALDEHYDE; ALLENE DERIVATIVE; CARBON; RUTHENIUM DERIVATIVE; SULFONAMIDE; ALKADIENE; AMINOALCOHOL; RUTHENIUM;

ALLYLATION; ARTICLE; CATALYST; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DIASTEREOISOMER; HYDROGENATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; CHEMISTRY; ISOMERISM;

ALDEHYDES; ALKADIENES; AMINO ALCOHOLS; HYDROGENATION; ISOMERISM; RUTHENIUM; SULFONAMIDES;

EID: 67849092737     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900827p     Document Type: Article

References (51)

1. For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: (a) Ngai, M.-Y.; Kong, J. R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
2. (b) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
3. (c) Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34.
4. For hydrogenative and transfer hydrogenative carbonyl vinylation employing nonconjugated alkynes as vinyl donors, see: (a) Rhee, J.-U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
5. (b) Skucas, E.; Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 7242.
6. (c) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
7. (d) Ngai, M.-Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644.
8. (e) Han, S. B.; Kong, J.-R.; Krische, M. J. Org. Lett. 2008, 10, 4133.
9. (f) Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066.
10. For hydrogenative carbonyl vinylation employing 1,3-enynes and 1,3-diynes as vinyl donors, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
11. (b) Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
12. (c) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
13. (d) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
14. (e) Hong, Y.-T.; Cho, C.-W.; Skucas, E.; Krische, M. J. Org. Lett. 2007, 9, 3745.
15. For carbonyl allylation via iridium-catalyzed hydrogenative and transfer hydrogenative coupling of dienes, allenes, and allyl acetate, see: (a) Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
16. (b) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134.
17. (c) Bower, J. F.; Patman, R. L.; Krische, M. J. Org. Lett. 2008, 10, 1033.
18. (d) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
19. (e) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.
20. (f) Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.
21. For carbonyl allylation via ruthenium-catalyzed transfer hydrogenative coupling of dienes and allenes, see: (a) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338.
22. (b) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120.
23. (c) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
24. For carbonyl propargylation via ruthenium-catalyzed transfer hydrogenative coupling of 1,3-enynes, see: Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 47, 5220.
25. For intermolecular aldol and Mannich addition via rhodium-catalyzed hydrogenative coupling of enones, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
26. (b) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
27. (c) Jung, C.-K.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 17051.
28. (d) Han, S. B.; Krische, M. J. Org. Lett. 2006, 8, 5657.
29. (e) Garner, S. A.; Krische, M. J. J. Org. Chem. 2007, 72, 5843.
30. (f) Bee, C.; Han, S. B.; Hassan, A.; Iida, H.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 2747.
31. For a review of the use of allenamides in organic synthesis, see: Wei, L.- L; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773.
32. For Ni-catalyzed allene-carbonyl reductive coupling, see ref 11a and: (a) Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320.
33. (b) Ng, S.- S.; Jamison, T. F. Tetrahedron 2005, 61, 11405.
34. (c) Ng, S.-S.; Jamison, T. F. Tetrahedron 2006, 62, 11350.
35. For intermolecular metal-catalyzed alkylative allene-carbonyl threecomponent coupling, see: (a) Anwar, U.; Grigg, R.; Rasparini, M.; Savic, V.; Sridharan, V. Chem. Commun. 2000, 645.
36. (b) Takimoto, M.; Kawamura, M.; Mori, M. Org. Lett. 2003, 5, 2599.
37. (c) Hopkins, C. D.; Malinakova, H. C. Org. Lett. 2004, 6, 2221.
38. (d) Hopkins, C. D.; Guan, L.; Malinakova, H. C. J. Org. Chem. 2005, 70, 6848.
39. (e) Hopkins, C. D.; Malinakova, H. C. Synthesis 2007, 3558.
40. For intramolecular metal-catalyzed alkylative allene-carbonyl threecomponent coupling, see: (a) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139.
41. (b) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009.
42. (c) Kang, S.-K.; Yoon, S.-K. Chem. Commun. 2002, 2634.
43. (d) Ha, Y.-H.; Kang, S.-K. Org. Lett. 2002, 4, 1143.
44. (e) Song, M.; Montgomery, J. Tetrahedron 2005, 61, 11440.
45. For carbonyl aminoallylation employing amino-substituted allylborane reagents, see: (a) Barrett, A. G. M.; Seefeld, M. A. J. Chem. Soc., Chem. Commun. 1993, 339.
46. (b) Barrett, A. G. M.; Seefeld, M. A. Tetrahedron 1993, 49, 7857.
47. (c) Barrett, A. G. M.; Seefeld, M. A.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1053.
48. (d) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677.
49. Trost, B. M.; Ferreira, E. M.; Gutierrez, A. C. J. Am. Chem. Soc. 2008, 130, 16176.
50. For related observations on ruthenium-mediated allene hydrometalation, see: (a) Bai, T.; Xue, P.; Sung, H. H.-Y.; Williams, I.; Ma, S.; Lin, Z.; Jia, G. Organometallics 2007, 26, 5581.
51. (b) Bai, T.; Ma, S.; Jia, G. Coord. Chem. Rev. 2009, 253, 423.