Enantioselective organo-SOMO catalysis: The α-vinylation of aldehydes

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 398-399

  Kim, Hahn ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; VINYL DERIVATIVE;

ALPHA VINYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; ENANTIOSELECTIVITY; ORGANO SOMO CATALYSIS; OXIDATION; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 40149110106     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077212h     Document Type: Article

References (21)

1. For seminal reports, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
2. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
3. For recent examples, see: (a) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
4. (b) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
5. (c) Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261.
6. (d) Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670.
7. (e) Aleman, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5520.
8. (f) Aleman, J.; Richter, B.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5515.
9. (a) Poulsen, T. B.; Bernardi, L.; Bell, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 6551.
10. (b) Chieffi, A.; Kamikawa, K.; Åhman, J.; Fox, J. M.; Buchwald, S. L. Org. Lett. 2001, 3, 1897.
11. (a) Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582.
12. (b) Jang, H.; Hong, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004.
13. Performed using B3LYP/6-311+G(2d,p)// B3LYP/6-31G(d). See ref 4a.
14. For recent reviews of trifluoroborate salt derivatives in synthesis, see: (a) Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49.
15. (b) Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623.
16. (c) Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2003, 22, 4313.
17. Elimination of boron via a β-radical intermediate (e.g., 3, eq 2) is a highly endothermic pathway and thereby presumed unlikely; see: Walton, J. C.; McCarroll, A. J.; Chen, Q.; Carboni, B.; Nziengui, R. J. Am. Chem. Soc. 2000, 122, 5455.
18. Kano, N.; Kawashima, T. In Modern Carbonyl Olefination; Takeda, T., Ed; Wiley-VCH: Weinheim, Germany, 2004; Chapter 2.
19. 4 reduction. See Supporting Information for details.
20. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765.
21. 1H NMR (400 MHz).