Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 300-310

  Kabir, M Shahjahan ^a   Namjoshi, Ojas A ^a   Verma, Ranjit ^a   Lorenz, Michael ^a   Phani Babu Tiruveedhula, V V N ^a   Monte, Aaron ^b   Bertz, Steven H ^c   Schwabacher, Alan W ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

^c UNIVERSITY OF NORTH CAROLINA AT CHARLOTTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-DIAZABICYCLO[2.2.2]OCTANE; ARYLOXY; CROSS COUPLING REACTIONS; ETHYL ACRYLATES; MEDICINAL CHEMISTRY; N-HETEROCYCLES; POLYMER INDUSTRIES; STEREOSPECIFIC MANNER; STEREOSPECIFIC SYNTHESIS;

CHEMICAL BONDS; PHENOLS; SALTS; SYNTHESIS (CHEMICAL);

ACRYLIC MONOMERS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACRYLIC ACID DERIVATIVE; ACRYLIC ACID ETHYL ESTER; AMINO ACID; BASE; NONMETAL; NUCLEOPHILE;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CONTROLLED STUDY; POLYMERIZATION; SCREENING; STEREOCHEMISTRY; STEREOSPECIFICITY; STOICHIOMETRY; SUBSTITUTION REACTION; SYNTHESIS;

ACRYLATES; AMINATION; CATALYSIS; COPPER; CROSS-LINKING REAGENTS; MOLECULAR STRUCTURE; PHENYL ETHERS; POLYMERS; STEREOISOMERISM;

EID: 84855565345     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201948e     Document Type: Article

References (37)

1. This work was presented previously in preliminary fashion, see: Kabir, M. S.; Namjoshi, O. A.; Verma, R.; Asad, M. S. A.; Lorenz, M.; Cook, J. M. Abstracts of Papers, 241st ACS National Meeting; Anaheim, CA, 2011; ORGN-188.
2. Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J.-F. Chem.-Eur. J. 2006, 12, 5301
3. Bao, W.; Liu, Y.; Lv, X. Synthesis 2008, 12, 1911
4. Ouali, A.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P.; Taillefer, M. J. Am. Chem. Soc. 2006, 128, 15990
5. Kaddouri, H.; Vicente, V.; Ouali, A.; Ouazzani, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 333
6. Kabir, M. S.; Lorenz, M.; Namjoshi, O. A.; Cook, J. M. Org. Lett. 2010, 12, 464-467
7. Kabir, M. S.; Namjoshi, O. A.; Verma, R.; Polanowski, R.; Krueger, S. M.; Sherman, D.; Rott, M, A.; Schwan, W. R.; Monte, A.; Cook, J. M. Bioorg. Med. Chem. 2010, 18, 4178
8. Neck, V. N.; Pannecouque, C.; Vanstreels, E.; Stevens, M.; Dehaen, W. Bioorg. Med. Chem. 2008, 16, 9487
9. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954 (Minireview) and references cited therein
10. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400 (Review) and references cited therein
11. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 115, 5558
12. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
13. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
14. Fraln, R.; Kikeji, D. Synthesis 2006, 2271
15. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651
16. Kienle, M.; Dubakka, S. R.; Brade, K.; Knochel, P. Eur. J. Org. Chem. 2007, 4166
17. Carril, M.; SanMartin, R.; Dominguez, E. Chem. Soc. Rev. 2008, 37, 639
18. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490
19. Altman, R. A.; Buchwald, S. L. Org. Lett. 2007, 9, 643
20. Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667
21. Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315
22. Harada, H.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2008, 73, 6772
23. Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978
24. Chemler, S. R.; Fuller, P. H. Chem Soc. Rev. 2007, 36, 1153
25. For a highlight on recent major developments in C-C, C-N and C-N coupling, please see: Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
26. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096 and references cited therein
27. Chen, Y.-G.; Chen, H.-H. Org. Lett. 2006, 8, 5609
28. Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809
29. Smith, A. B., III; Duffey, M. O.; Basu, K.; Walsh, S. P.; Suennemann, H. W.; Frohn, M. J. Am. Chem. Soc. 2008, 130, 422
30. Nicolaou, K. C.; Leung, G. Y. C.; Dethe, D. H.; Guduru, R.; Sun, Y. P.; Lim, C. S.; Chen, D. Y-K. J. Am. Chem. Soc. 2008, 130, 10019
31. Rodriguez, M.; Buchwald, S. L. Org. Lett. 2007, 9, 973
32. Shen, R.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Proco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889
33. Huang, X.; Shao, N.; Huryk, R.; Palani, A.; Aslanian, R.; Seidel-Dugan, C. Org. Lett. 2009, 11, 867
34. Cesati, R. R., III; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casebier, D. S. Org. Lett. 2007, 9, 5617. Other contributors were cited in the aforementioned referenced review and minireview
35. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005
36. Kabir, M. S.; Lorenz, M.; Van Linn, M. L.; Namjoshi, O. A.; Ara, S.; Cook, J. M. J. Org. Chem. 2010, 75, 3626
37. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161