Stereoselective Lewis acid-catalyzed α-acylvinyl additions

Journal of the American Chemical Society

Volumn 128, Issue 48, 2006, Pages 15382-15383

  Reynolds, Troy E ^a   Bharadwaj, Ashwin R ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33845298322     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0653674     Document Type: Article

References (49)

1. (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239-258.
2. (b) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326-1328.
3. (c) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
4. Chinchilla, R.; Najera, C. Chem. Rev. 2000, 100, 1891-1928.
5. (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.
6. For mechanistic studies, see: (b) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2005, 44, 1706-1708.
7. (c) Price K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980-3987.
8. (d) Krafft, M. E.; Haxell, T. F. N.; Seibert, K. A.; Abboud, K. A. J. Am. Chem. Soc. 2006, 128, 4174-4175.
9. Selected examples of enantioselective MBH reactions: (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318.
10. (b) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220.
11. (c) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094-12095.
12. (d) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. Also see ref 3a.
13. (a) Wang, L. C.; Luis, A. L.; Agaplou, K.; Jang, H. Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403.
14. (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405.
15. (c) Krafft, M. E.; Haxell, T. F. N. J. Am. Chem. Soc. 2005, 127, 10168-10169.
16. (a) Krause, N.; Hashmi, S. Modern Allene Chemistry; Wiley-VCH: Weinheim, Germany 2004.
17. (b) Krause, N.; Hoffmann-Roder, A. Tetrahedron 2004, 60, 11671-11694.
18. Kuwajima, I.; Kato, M. Tetrahedron Lett. 1980, 21, 623-626.
19. Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423-1424.
20. Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
21. (a) Merault, G.; Bourgeoi, P.; Dunogues, J.; Duffaut, N. J. Organomet. Chem. 1974, 76, 17-27.
22. (b) Fleming, I.; Perry, D. A. Tetrahedron 1981, 37, 4027-4034.
23. (c) Kato, M.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 827-830.
24. (d) Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-7800.
25. (e) Stergiades, I.; Tius, M. A J. Org. Chem. 1999, 64, 7547-7551.
26. (f) Li, G. G.; Wei, H. X.; Phelps, B. S.; Purkiss, D. W.; Kim, S. H. Org. Lett. 2001, 3, 823-826.
27. (g) Yoshizawa, K.; Shioiri, T. Tetrahedron Lett. 2006, 47, 757-761.
28. (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315.
29. (b) Myers, M. C.; Bharadwaj, A. R.; Milgram, B. C.; Scheidt, K. A. J. Am. Chem. Soc. 2005, 127, 14675-14680.
30. (c) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905-508.
31. (d) Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4932-4933.
32. For related approaches with racemic allenolates, see: (a) Sato, Y.; Takeuchi, S. Synthesis 1983, 734-735.
33. (b) Marino, J. P.; Linderman, R. J J. Org. Chem. 1983, 48, 4621-4628.
34. (c) Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037-1040.
35. (d) Ramachandran, P. V.; Rudd, M. T.; Burghardt, T. E.; Reddy, M. V. R. J. Org. Chem. 2003, 68, 9310-9316.
36. (e) Gudimalla, N.; Frohlich, R.; Höppe, D. Org. Lett. 2004, 6, 4005-4008.
37. (f) Xue, S.; He, L.; Han, K. Z.; Liu, Y. K.; Guo, Q. X. Synlett 2005, 1247-1250.
38. From propargyl alcohols, see: (g) Trost, B M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230-1231.
39. (h) Trost, B. M.; Chung, C. K. J. Am. Chem. Soc. 2006, 128, 10358-10359.
40. See Supporting Information for details.
41. 2O.
42. 3 as the Lewis acid did not afford product.
43. For reviews on asymmetric alkyne additions, see: (a) Pu, L. Tetrahedron 2003, 59, 9873-9886.
44. (b) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2004, 4095-4105.
45. For a recent addition of an alkyne to a glyoxylate-derived acylsilane in 64% ee and 30% yield, see: (c) Nicewicz, D. A.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 6170-6171.
46. Buckle, M. J. C.; Fleming, I.; Gil, S.; Pang, K. L. C. Org. Biomol. Chem. 2004, 2, 749-769.
47. The addition of 24 to benzaldehyde afforded 8 in 98% yield and 62:38 er.
48. (a) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882-2883.
49. (b) Ruck, R. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2003, 42, 4771-4774.