Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: Tandem aminoxylation/O-N bond heterolysis reactions

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1577-1580

  Ramachary, Dhevalapally B ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZENE DERIVATIVE; KETONE DERIVATIVE; NITROGEN; OXYGEN;

AMINOXYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; HETEROLYSIS; OPTICAL ROTATION; REDUCTION;

AMINES; AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; NITROSO COMPOUNDS; STEREOISOMERISM;

EID: 17844376726     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050246e     Document Type: Article

References (37)

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22. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
23. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
24. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
25. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
26. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
27. The 3b/trifluoroacetic acid (TFA) catalyst system was shown to be highly effective in the asymmetric aldol and Michael reactions. Due to the insolubility of salt 3b/TFA in other solvents, we used only DMSO as a solvent in our tandem ADS/O-N bond heterolysis studies. For details of catalyst 3b/TFA in asymmetric catalysis, see: (a) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527-2530. (b) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372. (d) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F., III. J. Org. Chem. 2004, 69, 5838-5849. (e) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (g) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
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