Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: Asymmetric synthesis of β,γ-unsaturated α-hydroxy esters

Organic Letters

Volumn 9, Issue 19, 2007, Pages 3745-3748

  Hong, Young Taek ^a   Cho, Chang Woo ^a,b   Skucas, Eduardas ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b Kyungpook National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHYLENE; ETHYLENE DERIVATIVE; HYDROGEN; OXALIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ESTERS; ETHYLENES; HYDROGEN; MOLECULAR STRUCTURE; OXALATES; STEREOISOMERISM;

EID: 34848878354     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7015548     Document Type: Article

References (65)

1. Fischer, F.; Tropsch, H. Brennstoff Chem. 1923, 4, 276.
2. (b) Fischer, F.; Tropsch, H. Chem. Ber. 1923, 56B, 2428.
3. (c) Roelen, O. German Patent DE 1938, 849,548.
4. For recent reviews, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
5. (b) Iida, H.; Krische, M. J. Top. Cur. Chem. 2007, 279, 77.
6. For hydrogen-mediated reductive aldol and Mannich couplings, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
7. (b) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.
8. (c) Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.
9. (d) Marriner, G. A.; Garner, S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.
10. (e) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
11. (f) Han, S. B.; Krische, M. J. Org. Lett. 2006, 8, 5657.
12. (g) Jung, C.-K.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 17051.
13. (h) Garner, S. A.; Krische, M. J. J. Org. Chem. 2007, 72, 5843.
14. For hydrogen-mediated couplings of alkenes to carbonyl compounds, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 4074.
15. (b) Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem., Int. Ed. 2006, 128, 6885. Also see ref 7b.
16. For hydrogen-mediated couplings of alkynes to carbonyl compounds and imines, see: (a) Huddleston, R. R.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 11488.
17. (b) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
18. (c) Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
19. (d) Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 891.
20. (e) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
21. (f) Cho, C.-W.; Krische, M. J. Org. Lett. 2006, 8, 3873.
22. (g) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
23. (h) Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16040.
24. (i) Ngai, M.-Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 280.
25. (j) Skucas, E.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 7242.
26. (k) Barchuk. A.: Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
27. For hydrogen-mediated carbocyclizations, see: (a) Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 7875.
28. (b) Jang, H.-Y.; Hughes, F. W.; Gong, H.; Zhang, J.; Brodbelt, J. S.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 6174.
29. (c) Rhee, J.-U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
30. (d) Jung, I. G.; Seo, J.; Lee, S. I.; Choi, Y.; Chung, Y. K. Organometallics 2006, 25, 4240.
31. (e) Smith, D. M.; Pulling, M. E.; Norton, J. R. J. Am. Chem. Soc. 2007, 129, 770 and ref 7a.
32. Prior to our work, two isolated examples of hydrogen-mediated C-C bond formation that did not involve couplings to carbon monoxide were reported: (a) Molander, G. A.; Hoberg, J. O J. Am. Chem. Soc. 1992, 114, 3123.
33. (b) Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1995, 14; 4521.
34. Indirect asymmetric alkyne-aldehyde reductive coupling has been achieved via stoichiometric alkyne hydrometallation (hydroboration or hydrozirconation) followed by transmetallation to afford vinylzinc reagents, which engage in enantioselective catalytic additions to aldehydes; see: (a) Oppolzer, W.; Radinov, R. Helv. Chim. Acta 1992, 75, 170.
35. (b) Oppolzer, W.; Radinov, R. J. Am. Chem. Soc. 1993, 115. 1593.
36. (c) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257.
37. (d) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
38. (e) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36. 2607.
39. (f) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
40. (g) Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766.
41. (h) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
42. (i) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225.
43. (j) Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589.
44. (k) Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 10677.
45. (l) Ko, D.-H.; Kang. S.-W.; Kim, K. H.; Chung, Y.; Ha, D.-C. Bull. Kor. Chem. Soc. 2004, 25, 35.
46. (m) Sprout, C. M.; Richmond, M. L.; Seto, C. T. J. Org. Chem. 2004, 69, 6666.
47. (n) Jeon, S.-J.; Chen, Y. K.; Walsh, P. J. Org. Lett. 2005, 7, 1729.
48. (o) Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2006, 128, 9618.
49. (p) Lauterwasser, F.; Gall, J.; Hoefener, S.; Bräse, S. Adv. Synth. Catal. 2006, 348, 2068.
50. For indirect catalytic enantioselective alkyne-ketone reductive couplings analogous to those described in the preceding reference, see: (a) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538.
51. (b) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355.
52. (c) Jeon, S.-J.; Li, H.; Garcia, C.; La Rochelle, L. K.; Walsh, P. J. J. Org. Chem. 2005, 70, 448.
53. Direct alkyne-aldehyde reductive coupling to furnish allylic alcohols has been achieved under the conditions of nickel catalysis: see: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
54. (b) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221.
55. (c) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
56. (d) For enyne coupling, see: Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 4130.
57. (e) Miller, K. M.; Jamison, T. F. Org. Lett. 2005, 7, 3077.
58. (a) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
59. (b) For a review, see: Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63.
60. (a) Lemieux; R. U.; von Rudloff, E. Can. J. Chem. 1955, 33, 1701.
61. (b) Pappo, R.; Allen, D. S., Jr.; Lemieux;, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
62. (a) Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Organomet. Chem. 1977, 141, 205.
63. (b) For a review, see: Crabtree, R. H. Acc. Chem. Res. 1979, 12, 331.
64. (c) For hydrogenation of conjugated dienes catalyzed by iridium, see: Cui, X.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14212.
65. Funk, T. W.; Efskind, J.; Grubbs, R. H. Org. Lett. 2005, 7, 187.