The Petasis reaction: Microscale synthesis of a tertiary amine antifungal analog

Journal of Chemical Education

Volumn 89, Issue 6, 2012, Pages 796-798

  Koroluk, Katherine J ^a   Jackson, Derek A ^a   Dicks, Andrew P ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Amines Ammonium Compounds; Chirality Optical Activity; Combinatorial Chemistry; Drugs Pharmaceuticals; Hands On Learning Manipulatives; Laboratory Instruction; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Upper Division Undergraduate

Indexed keywords

EID: 84860743312     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed200426m     Document Type: Article

References (30)

1. McMurry, J. Organic Chemistry, 8 th ed.; Thomson Higher Education: Belmont, CA, 2012; p 956.
2. Carlson, M. W.; Ciszewski, J. T.; Bhatti, M. M.; Swanson, W. F.; Wilson, A. M. J. Chem. Educ. 2000, 77, 270-271
3. Saba, S.; Ciaccio, J. A.; Espinal, J.; Aman, C. E. J. Chem. Educ. 2007, 84, 1011-1013
4. Crouch, R. D.; Holden, M. S.; Weaver, T. M. Chem. Educator 1998, 3, DOI: 10.1333/s00897980205a.
5. Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583-586
6. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169-6193
7. Batey, R. A. Nucleophilic Addition Reactions Of Aryl And Alkenylboronic Acids And Their Derivatives To Imines And Iminium Ions. In Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 279-304.
8. Petasis, N. A.; Boral, S. Tetrahedron Lett. 2001, 42, 539-542
9. Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron 2000, 56, 10023-10030
10. Voisin, A. S.; Bouillon, A.; Lancelot, J.-C.; Lesnard, A.; Oulyadi, H.; Rault, S. Tetrahedron Lett. 2006, 47, 2165-2169
11. Tao, J.; Li, S. Chin. J. Chem. 2010, 28, 41-49
12. Petranyi, G.; Georgopoulos, A.; Mieth, H. Antimicrob. Agents Chemother. 1981, 19, 390-392
13. Krishnan-Natesan, S. Expert Opin. Pharmacother. 2009, 10, 2723-2733
14. Greening the Organic Curriculum: Development of an Undergraduate Catalytic Chemistry Course. www.ccce.divched.org/P5Spring2010ConfChem (accessed Mar 2012).
15. Sigma-Aldrich Home Page. www.sigmaaldrich.com (accessed Mar 2012).
16. Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Tables of Spectral Data, 3 rd ed.; Springer-Verlag: Berlin, 2000; p 249.
17. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515
18. Field, L. D.; Sternhell, S.; Kalman, J. R. Organic Structures from Spectra, 3 rd ed.; Wiley: New York, NY, 2002; p 59.
19. Aktoudianakis, E.; Lin, R. J.; Dicks, A. P. J. Chem. Educ. 2006, 83, 1832-1834
20. Davenport, D. A. J. Chem. Educ. 1981, 58, 682-683
21. McMurry, J. Organic Chemistry, 8 th ed.; Thomson Higher Education: Belmont, CA, 2012; pp 165-166.
22. Smith, J. G. Organic Chemistry, 3 rd ed.; McGraw-Hill: New York, NY, 2011; p 951.
23. Liu, Y.; Wang, L.; Sui, Y.; Yu, J. Chin. J. Chem. 2010, 28, 2039-2044
24. Candeias, N. R.; Veiros, L. F.; Afonso, C. A. M.; Gois, P. M. P. Eur. J. Org. Chem. 2009, 1859-1863
25. Candeias, N. R.; Cal, P. M. S. D.; André, V.; Duarte, M. T.; Veiros, L. F.; Gois, P. M. P. Tetrahedron 2010, 66, 2736-2745
26. Nun, P.; Martinez, J.; Lamaty, F. Synthesis 2010, 12, 2063-2068
27. Jourdan, H.; Gouhier, G.; Van Hijfte, L.; Angibaud, P.; Piettre, S. R. Tetrahedron Lett. 2005, 46, 8027-8031
28. Yadav, J. S.; Reddy, B. V. S.; Naga Lakshmi, P. N. J. Mol. Catal. A: Chem. 2007, 274, 101-104
29. Trost, B. M. Science 1991, 254, 1471-1477
30. Neogi, S.; Roy, A.; Naskar, D. J. Comb. Chem. 2010, 12, 617-629