The use of pH to influence regio- and chemoselectivity in the asymmetric aminohydroxylation of styrenes

Organic Letters

Volumn 5, Issue 3, 2003, Pages 281-284

  Nesterenko, Vitaliy ^a   Byers, Joshua T ^a   Hergenrother, Paul J ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMATE NITROGEN; CARBAMIC ACID DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINOHYDROXYLATION; ARTICLE; CHEMICAL REACTION; ENANTIOSELECTIVITY; ISOMER; PH; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE SENSITIVITY;

EID: 0141518298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027242j     Document Type: Article

References (18)

1. (a) Li, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
2. (b) O'Brien, P. Angew. Chem., Int. Ed. 1999, 38, 326-329.
3. (a) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507-2510.
4. (b) Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949-1952.
5. (c) Han, H.; Cho, C.-W.; Janda, K. D. Chem. Eur. J. 1999, 5, 1565-1569.
6. (a) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207-1217.
7. (b) O'Brien, P.; Osborne, S. A.; Parker, D. D. J. Chem. Soc., Perkin Trans. 1 1998, 2519-2526.
8. (c) Goossen, L. J.; Liu, H.; Dress, K. R.; Sharpless, K. B. Angew. Chem., Int. Ed. 1999, 38, 1080-1083.
9. (d) Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221-2223.
10. (e) Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 3667-3670.
11. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. 1997, 36, 1483-1486.
12. For recent studies on the pH dependence of the asymmetric dihyroxylation see: (a) Krief, A.; Castillo-Colaux, C. Synlett 2001, 501-504. (b) Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421-434.
13. For recent studies on the pH dependence of the asymmetric dihyroxylation see: (a) Krief, A.; Castillo-Colaux, C. Synlett 2001, 501-504. (b) Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421-434.
14. Dobler, C.; Mehltretter, G.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 3026-3028.
15. Wuts, P. G. M.; Anderson, A. M.; Goble, M. P.; Mancini, S. E.; VanderRoest, R. J. Org. Lett. 2000, 2, 2667-2669.
16. For use of less sterically challenged nitrogen sources in the asymmetric aminohydroxylation see: Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810-2813.
17. (a) Menard, H.; Lessard, J. J. Chem. Eng. Data 1978, 23, 64-65.
18. (b) Bachand, C.; Driguez, H.; Paton, J. M.; Touchard, D.; Lessard, J. J. Org. Chem. 1974, 39, 3136-3138.