Enantioselective addition of vinylzinc reagents to aldehydes catalyzed by modular ligands derived from amino acids

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 8835-8840

  Richmond, Meaghan L ^a   Sprout, Christopher M ^a   Seto, Christopher T ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; AROMATIC COMPOUNDS; CATALYSIS; CRYSTALLIZATION; PROTEINS; SCANNING; SYNTHESIS (CHEMICAL); VINYL RESINS;

BOC-PROTECTED AMINO ACIDS; N-ACYLETHYLENEDIAMINE-BASED LIGANDS; POSITIONAL SCANNING APPROACH; VINYLZINC REAGENTS;

ALDEHYDES;

4,4 DIMETHYL 1 (NAPHTHALENE 1 YL)PENT 2 EN 1 OL; ALDEHYDE; ALKYNE; ALLYL ALCOHOL; AMIDE; AMINO ACID; BENZALDEHYDE; CARBAMIC ACID DERIVATIVE; LIGAND; MACROGOL; NAPHTHALENE DERIVATIVE; PYRROLIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALDEHYDES; AMIDES; AMINO ACIDS; CARBAMATES; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; STEREOISOMERISM; VINYL COMPOUNDS; ZINC;

EID: 27444438173     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051313l     Document Type: Article

References (43)

1. For recent examples, see: (a) Drutu, I.; Krygowski, E. S.; Wood, J. L. J. Org. Chem. 2001, 66, 7025-7029.
2. (b) Griesbeck, A. G.; El-Idreesy, T. T.; Fiege, M.; Brun, R. Org. Lett. 2002, 4, 4193-4195.
3. (c) Lambert, W. T.; Burke, S. D. Org. Lett. 2003, 5, 515-518.
4. (d) Yun, H.; Danishefsky, S. J. J. Org. Chem. 2003, 68, 4519-4522.
5. (e) Weaving, R.; Roulland, E.; Monneret, C.; Florent, J.-C. Tetrahedron Lett. 2003, 44, 2579-2581.
6. (f) Smith, T. E.; Djang, M.; Velander, A. J.; Downey, C. W.; Carroll, K. A.; van Alphen, S. Org. Lett. 2004, 6, 2317-2320.
7. For recent examples, see: (a) van der Berg, R. J. B. H. N.; Korevaar, C. G. N.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. J. Org. Chem. 2004, 69, 5699-5704.
8. (b) Barboni, L.; Giarlo, G.; Ricciutelli, M.; Ballini, R.; Georg, G. I.; VanderVelde, D. G.; Himes, R. H.; Wang, M.; Lakdawala, A.; Snyder, J. P. Org. Lett. 2004, 6, 461-464.
9. (c) Zannatta, S. D.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1041-1044.
10. (d) Magnin-Lachaux, M.; Tan, Z.; Liang, B.; Negishi, E.-I. Org. Lett. 2004, 6, 1425-1427.
11. (e) Wu, Y.; Shen, X.; Yang, Y.-Q.; Hu, Q.; Huang, J.-H. J. Org. Chem. 2004, 69, 3857-3865.
12. (f) Vassilikogiannakis, G.; Margaros, I.; Montagnon, T. Org. Lett. 2004, 6, 2039-2042.
13. (g) Mehta, G.; Roy, S. Org. Lett. 2004, 6, 2389-2392.
14. (h) Rai, A. N.; Basu, A. Org. Lett. 2004, 6, 2861-2863.
15. (i) El Sous, M.; Ganame, D.; Tregloan, P. A.; Rizzacasa, M. A. Org. Lett. 2004, 6, 3001-3004.
16. (j) Morales, C. A.; Layton, M. E.; Shair, M. D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12036.
17. Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197-5200.
18. (a) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333-340.
19. (b) Labinger, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol 8, pp 667-702.
20. (a) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455.
21. (b) Wipf, P.; Jayasuriya, N.; Ribe, S. Chirality 2003, 15, 208-212.
22. (c) Wipf, P.; Kendall, C. Chem. Eur. J. 2002, 8, 1778-1784.
23. Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173.
24. (a) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648.
25. (b) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777-5780.
26. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593-1594.
27. (d) Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766-4770.
28. Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119-4122.
29. Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589-1590.
30. Tseng, S.-L.; Yang, T.-K. Tetrahedron: Asymmetry 2005, 16, 773-782.
31. (a) Nugent, W. A. J. Chem. Soc., Chem. Commun. 1999, 1369-1370.
32. (b) Rosner, T.; Sears, P. J.; Nugent, W. A.; Blackmond, D. G. Org. Lett. 2000, 2, 2511-2513.
33. Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225-12231.
34. Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 10677-10683.
35. Jeon, S.-J.; Chen, Y. K.; Walsh, P. J. Org. Lett. 2005, 7, 1729-1732.
36. Lurain, A. E.; Carroll, P. J.; Walsh, P. J. J. Org. Chem. 2005, 70, 1262-1268.
37. Richmond, M. L.; Seto, C. T. J. Org. Chem. 2003, 68, 7505-7508.
38. Sprout, C. M.; Seto, C. T. J. Org. Chem. 2003, 68, 7788-7794.
39. 1H NMR spectrum of a mixture of diethylzinc and a related N-acylethylenediamine-based ligand shows disappearance of the NH protons and formation of ethane. See ref 17.
40. Sprout, C. M.; Richmond, M. R.; Seto, C. T. J. Org. Chem. 2004, 69, 6666.
41. For the synthesis and characterization of amides 2a,b,h-i and ligands 3a,b,h,i, and 4d-i, see ref 16.
42. Rudolph, J.; Hermanns, N.; Bolm, C. J. Org. Chem. 2004, 69, 3997-4000.
43. Dahmen, S. Org. Lett. 2004, 6, 2113-2116.