The importance of iminium geometry control in enamine catalysis: Identification of a new catalyst architecture for aldehyde-aldehyde couplings

Angewandte Chemie - International Edition

Volumn 43, Issue 48, 2004, Pages 6722-6724

  Mangion, Ian K ^a   Northrup, Alan B ^a   MacMillan, David W C ^a  

^a California Institute of Technology   (United States)

Author keywords

Aldehydes; Aldol reaction; Nitrogen heterocycles; Organocatalysis; Synthetic methods

Indexed keywords

ALDEHYDES; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOCHEMISTRY;

ALDOL DONOR; ENANTIOSELECTIVITY; IMINIUM; ORGANOCATALYST SYSTEM;

CATALYSIS;

ALDEHYDE; ENAMINE; IMINE; TRIFLUOROACETIC ACID;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; GEOMETRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALDEHYDES; AMINES; CATALYSIS; IMIDAZOLIDINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 10944233787     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461851     Document Type: Article

References (23)

1. "Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds": a) Z. G. Hajos, D. R. Parrish, German Patent DE2102623, July 29, 1971;
2. b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615.
3. a) "Optically active 1,5-Indanone and 1,6-Naphthalenedione": U. Eder, G. Sauer, R. Wiechert (Schering AG), German Patent DE 2014757, Oct. 7, 1971;
4. b) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496.
5. b) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496.
6. a) K. Sakthievel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
7. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386.
8. For examples of metal-mediated direct aldol reactions, see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
9. For examples of metal-mediated direct aldol reactions, see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
10. b) N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Oshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466;
11. d) N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Oshima, M. Shibasaki, Org. Lett. 2001, 3, 1539;
12. e) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003;
13. f) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497;
14. g) D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392.
15. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798.
16. S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 11273.
17. a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
18. b) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172.
19. 2O: 86% yield, 4:1 anti/syn, 94% ee; dioxane: 92% yield, 4:1 anti/syn, 94% ee.
20. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152.
21. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152.
22. A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752.
23. We recently determined that this imidazolidinone-catalyzed aldol reaction allows enantioselective access to gulose in two steps.