Kinetic analysis of the divergence of reaction pathways in the chiral Lewis base promoted aldol additions of trichlorosilyl enol ethers: A Rapid-injection NMR study

Helvetica Chimica Acta

Volumn 83, Issue 8, 2000, Pages 1846-1853

  Denmark, Scott E ^a   Pham, Son M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; ENTHALPY; ENTROPY; KINETICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033843536     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000809)83:8<1846::AID-HLCA1846>3.0.CO;2-V     Document Type: Article

References (17)

1. a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404;
2. b) S. E. Denmark, K.-T. Wong, R. A. Stavenger, J. Am. Chem. Soc. 1997, 119, 2333;
3. c) S. E. Denmark, R. A. Stavenger, K.-T. Wong, J. Org. Chem. 1998, 63, 918;
4. d) S. E. Denmark, R. A. Stavenger, S. B. W. Winter, K.-T. Wong, P. A. Barsanti, J. Org. Chem. 1998, 63, 9517;
5. e) S. E. Denmark, X. Su, Y. Nishigaichi, J. Am. Chem. Soc. 1998, 120, 12990;
6. f) S. E. Denmark, R. A. Stavenger, K.-T. Wong, X. Su, J. Am. Chem. Soc. 1999, 121, 4982;
7. g) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 132.
8. a) D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, H. B. Kagan, J. Am. Chem. Soc. 1994, 116, 9430;
9. b) D. R. Fenwich, H. B. Kagan, Top. Stereochem. 1999, 22, 257;
10. c) C. Girard, H. B. Kagan, Angew. Chem., Int. Ed. 1998, 22, 2922;
11. d) M. Avalos, R. Babiano, P. Cintas, J. L. Jimenez, J. C. Palacios, Tetrahedron: Asymmetry 1997, 8, 2997.
12. a) A. G. Myers, K. L. Widdowson, J. Am. Chem. Soc. 1990, 112, 9672;
13. b) A. G. Myers, K. L. Widdowson, P. J. Kukkola, J. Am. Chem. Soc. 1992, 114, 2765;
14. c) B. W. Gung, Z. Zhu, R. A. Fouch, J. Org. Chem. 1995, 60, 2860.
15. a) J. F. McGarrity, J. Prodolliet, T. Smyth, Org. Magn. Reson. 1981, 17, 59;
16. b) C. A. Palmer, C. A. Ogle, E. M. Arnett, J. Am. Chem. Soc. 1992, 114, 5619;
17. c) M. T. Reetz, B. Raguse, C. F. Marth, H. M. Hügel, T. Bach, D. N. A. Fox, Tetrahedron 1992, 48, 5731.