Diastereoselectivity in the reduction of α-hydroxyketones: An experiment for the chemistry major organic laboratory

Journal of Chemical Education

Volumn 83, Issue 1, 2006, Pages 101-105

  Ball, David B ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMISTRY; CURRICULA; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; STUDENTS; SYNTHESIS (CHEMICAL); THIN LAYER CHROMATOGRAPHY;

DIASTEREOSELECTIVITY; HYDROXYKETONES; ORGANIC CHEMISTRY;

KETONES;

EID: 30344470754     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed083p101     Document Type: Article

References (25)

1. Ball, D. B.; Miller, R.J. Chem. Educ. 2002, 79, 665-666.
2. (a) Ball, D. B.; Miller, R. M. J. Chem. Educ. 2004, 81, 121-125.
3. (b) Ball, D. B.; Wilson, R. J. Chem. Educ. 2002, 79, 112-115.
4. (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin, Inc.: Menlo Park, CA, 1972; pp 45-70.
5. (b) Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis; ACH: New York, 1991; Chapter 2.
6. (a) Richardson, D. P.; Wilson, W.; Mattson, R. J.; Powers, D. M; Dolan, B. T. J. Chem. Educ. 1991, 68, 951-955.
7. (b) Depres, J.-P.; Morat, C. J. Chem. Educ. 1992, 69, A232-A239.
8. (c) Ciaccio, J. A.; Bravo, R. P.; Drahus, A. L.; Biggans, J. B.; Concepcion, R. V.; Cagrera, D. J. Chem. Educ. 2001, 78, 531-533.
9. (a) Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; American chemical Society: Washington DC, 1976; pp 84-132.
10. (b) Cram, D. J.; AbdElhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5824.
11. (c) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748.
12. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 875-880.
13. (e) Stocker, J. H.; Sidisunthorn, P.; Benjamin, B. M.; Collins, C. J. J. Am. Chem. Soc. 1960, 82, 3913.
14. (f) Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245.
15. (g) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
16. (h) Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205.
17. Corey, E. J.; Cheng, X. The Logic of Cbemical Synthesis; John Wiley & Sons: New York, 1989; pp 1-16.
18. Smith, M. B. Organic Synthesis, 2nd ed.; McGraw Hill: New York, 2002; pp 633-642.
19. Narasimhan, S.; Balakumar, R. Aldrichimica Acta 1998, 31, 19-26.
20. Shaka, A. J. J. Magn. Res. 1997, 125, 302-324.
21. (a) Nakata, T.; Tanaka, T.; Oishi, T. Tetrahedron Lett. 1983, 24, 2653-2656.
22. (b) Katzenellenbogen, J. A.; Bowlus, S. B. J. Org. Chem. 1973, 38, 627-632.
23. (c) Katzenellenbogen, J. A.; Bowlus, S. B. J. Org. Chem. 1974, 39, 3309-3314.
24. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065.
25. Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563. 30, 1563