Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes

Journal of the American Chemical Society

Volumn 126, Issue 13, 2004, Pages 4108-4109

  Brochu, Michael P ^a   Brown, Sean P ^a   MacMillan, David W C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE;

AMINATION; ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; CHLORINATION; CYCLIZATION; ENANTIOSELECTIVITY; HALOGENATION; SYNTHESIS;

EID: 1842450587     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049562z     Document Type: Article

References (22)

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2. (b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J., III; Lectka, T. Org. Lett. 2001, 3, 2049.
3. Lewis acid-catalyzed asymmetric halogenation of β-keto esters: (c) Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359.
4. (d) Hintermann, L.; Togni, A. Helv. Chim. Acta 2000, 83, 2425.
5. Auxiliary-based route to α-chloroimides: (e) Evans, D. A.; Ellman, J. A.; Dorow, R. L. Tetrahedron Lett. 1987, 28, 1123.
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9. (c) De Kimpe, N.; Verhé, R. The Chemistry of α-Haloketones, (α-Haloaldehydes, and α-Haloimines; John Wiley & Sons: New York, 1990.
10. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
11. (b) Northrup, A. B.; MacMillan. D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
12. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
13. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
14. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
15. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
16. Mukaiyama - Michael reaction: (g) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
17. Direct aldehyde - aldehyde aldol: (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
18. Brown, S, P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808.
19. Two groups have reported similar studies: (a) Zhong, G. Angew. Chem. 2003, 115, 4379.
20. (b) Hayashi, Y.; Yamaguchi, J.; Hibino. K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293.
21. Iatrobeads 6RS-8060 from latron Laboratories, Inc., 11-4 Higashi-Kanda 1-Chrome, Chiyoda-Ku, Tokyo 101, Japan.
22. 4+3 cycloaddition: Harmata, M.; Ghosh, S, K.; Hong, X.; Wacharasindhu, S.; Kirchhoefer, P. J. Am. Chem. Soc. 2003, 125, 2058.