Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2591-2593

  Chin, Jik ^a   Dong, Chan Kim ^b   Kim, Hae Jo ^a   Panosyan, Francis B ^a   Kwan, Mook Kim ^c  

^a UNIVERSITY OF TORONTO   (Canada)

^b Korea Institute of Science and Technology   (South Korea)

^c Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; AMINO ACID DERIVATIVE; IMINE;

ARTICLE; CHIRALITY; ENANTIOMER; EQUILIBRIUM CONSTANT; EVALUATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

ALDEHYDES; AMINO ACIDS; HYDROGEN BONDING; IMINES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4043095002     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049084x     Document Type: Article

References (28)

1. Wenzel, T. J.; Wilcox, J. D. Chirality 2003, 15, 256-270.
2. Parker, D. Chem. Rev. 1991, 91, 1441-1457.
3. Sullivan, G. R. Top. Stereochem. 1978, 10, 287-329.
4. (a) Hulst, R.; de Vries, N. K.; Feringa, B. L. T J. Org. Chem. 1994, 59, 7453-7458.
5. (b) Watanabe, M.; Hasegawa, T.; Miyake, H.; Kojima, Y. Chem. Lett. 2001, 4-5.
6. (c) Wenzel, T. J.; Miles, R. D.; Zomlefer, K.; Frederique, D. E.; Roan, M. A.; Troughton, J. S.; Pond, B. V.; Colby, A. L. Chirality 2000, 12, 30-37.
7. (a) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344-1346.
8. (b) Böhm, A.; Seebach, D. Helv. Chim. Acta 2000, 83, 3262-3278.
9. (a) Claeys-Bruno, M.; Bardet, M.; Marchon, J.-C. Magn. Reson. Chem. 2002, 40, 647-652.
10. (b) Claeys-Bruno, M.; Toronto, D.; Pecaut, J.; Bardet, M.; Marchon, J.-C. J. Am. Chem. Soc. 2001, 123, 11067-11068.
11. (a) Wenzel, T. J.; Thurston, J. E. Tetrahedron Lett. 2000, 41, 3769-3772.
12. (b) Seco, J. M.; Quińoá, E.; Riguera, R. J. Org. Chem. 1999, 64, 4669-4675.
13. (c) Seco, J. M.; Latypov, S. K.; Quińoá, E.; Riguera, R. J. Org. Chem. 1997, 62, 7569-7574.
14. (d) Chinchilla, R.; Favello, L. R.; Nájera, C. J. Org. Chem. 1996, 61, 7285-7290.
15. (e) Pirkle, W. H.; Beare, S. D. J. Am. Chem. Soc. 1969, 91, 5150-5155.
16. (f) Dufrasne, F.; Gelbcke, M.; Neve, J. Spectrochim. Acta 2003, A59, 1239-1245.
17. 31P NMR: (a) Hulst, R.; Zijlstra, R. W. J.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 1701-1710. (b) Hulst, R.; de Vries, N. K.; Feringa, B. L. T Angew. Chem., Int. Ed. Engl. 1992, 31, 1092-1093. (c) Kruizinga, W. H.; Bolster, J.; Kellog, R. M. J. Org. Chem. 1988, 53, 1826-1827.
18. 31P NMR: (a) Hulst, R.; Zijlstra, R. W. J.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 1701-1710. (b) Hulst, R.; de Vries, N. K.; Feringa, B. L. T Angew. Chem., Int. Ed. Engl. 1992, 31, 1092-1093. (c) Kruizinga, W. H.; Bolster, J.; Kellog, R. M. J. Org. Chem. 1988, 53, 1826-1827.
19. 31P NMR: (a) Hulst, R.; Zijlstra, R. W. J.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 1701-1710. (b) Hulst, R.; de Vries, N. K.; Feringa, B. L. T Angew. Chem., Int. Ed. Engl. 1992, 31, 1092-1093. (c) Kruizinga, W. H.; Bolster, J.; Kellog, R. M. J. Org. Chem. 1988, 53, 1826-1827.
20. Amino acid analysis by deuterium NMR: (a) Chalard, P.; Bertrand, M.; Canet, I.; Théry, V.; Remuson, R.; Jeminet, G. Org. Lett. 2000, 2, 2431-2434. (b) Meddour, A.; Loewenstein, A.; Péchiné, J.-M.; Courtieu, J. Tetrahedron: Asymmetry 1997, 8, 485-494. (c) Canet, I.; Meddour, A.; Courtieu, J.; Canet, J. L.; Salaün, J. J. Am. Chem. Soc. 1994, 116, 2155-2156.
21. Amino acid analysis by deuterium NMR: (a) Chalard, P.; Bertrand, M.; Canet, I.; Théry, V.; Remuson, R.; Jeminet, G. Org. Lett. 2000, 2, 2431-2434. (b) Meddour, A.; Loewenstein, A.; Péchiné, J.-M.; Courtieu, J. Tetrahedron: Asymmetry 1997, 8, 485-494. (c) Canet, I.; Meddour, A.; Courtieu, J.; Canet, J. L.; Salaün, J. J. Am. Chem. Soc. 1994, 116, 2155-2156.
22. Amino acid analysis by deuterium NMR: (a) Chalard, P.; Bertrand, M.; Canet, I.; Théry, V.; Remuson, R.; Jeminet, G. Org. Lett. 2000, 2, 2431-2434. (b) Meddour, A.; Loewenstein, A.; Péchiné, J.-M.; Courtieu, J. Tetrahedron: Asymmetry 1997, 8, 485-494. (c) Canet, I.; Meddour, A.; Courtieu, J.; Canet, J. L.; Salaün, J. J. Am. Chem. Soc. 1994, 116, 2155-2156.
23. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 124, 10405-10417.
24. Chin, J.; Mancin, F.; Thavarajah, N.; Lee, D.; Lough, A.; Chung, D. S. J. Am. Chem. Soc. 2003, 127, 15276-15277.
25. Molecular mechanics computation was performed using Spartan '02 Windows from Wavefunction, Inc.
26. (a) Kim, H. C.; Choi, S.; Kim, H.; Ahn, K.-H. Tetrahedron Lett. 1997, 38, 3959-3962.
27. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252-2260.
28. See Supporting Information.