A mechanistic investigation of the asymmetric Meerwein-Schmidt-Ponndorf- Verley reduction catalyzed by BINOL/AlMe3 - Structure, kinetics, and enantioselectivity

Journal of Organic Chemistry

Volumn 72, Issue 24, 2007, Pages 9121-9133

  Graves, Christopher R ^a   Zhou, Hongying ^a   Stern, Charlotte L ^a   Nguyen, SonBinh T ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; MICROSTRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS;

2-POINT COORDINATION; CATALYST LOADING; LIGAND-ACCELERATED CATALYSIS; MEERWEIN-SCHMIDT-PONNDORF-VERLEY (MSPV);

SELECTIVE CATALYTIC REDUCTION;

2 PROPANOL; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALUMINUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MEERWEIN PONNDORF VERLEY REDUCTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 36649013412     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070563u     Document Type: Article

References (48)

1. Verley, M. Bull. Soc. Chim. Fr. 1925, 37, 871-874.
2. Ponndorf, W. Angew. Chem. 1926, 39, 138-143.
3. Meerwein, H.; Schmidt, R. Justus Liebigs Ann. Chem. 1925, 444, 221-238.
4. Graves, C. R.; Campbell, E. J.; Nguyen, S. T. Tetrahedron: Asymmetry 2005, 16, 3460-3468.
5. Wilds, A. L. Org. React. 1944, 2, 178-223.
6. de Graauw, C. F.; Peters, J. A.; van Bekkum, H.; Huskens, J. Synthesis 1994, 1007-1017.
7. Aldrige, S.; Downs, A. J. Chem. Rev. 2001, 101, 3305-3366.
8. Akamanchi, K. G.; Noorani, V. R. Tetrahedron Lett. 1995, 36, 5085-5088.
9. Kow, R.; Nygren, R.; Rathke, M. W. J. Org. Chem. 1977, 42, 826-827.
10. Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. 1998, 37, 2347-2349.
11. Ooi, T.; Itagaki, Y.; Miura, T.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2137-2138.
12. Ooi, T.; Miura, T.; Itagaki, Y.; Ichikawa, H.; Maruoka, K. Synthesis 2002, 279-291.
13. Ooi, T.; Takahashi, M.; Yamada, M.; Tayama, E.; Omoto, K.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 1150-1160.
14. Konishi, K.; Makita, K.; Aida, T.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 643-645.
15. Liu, Y.-C.; Ko, B.-T.; Huang, B.-H.; Lin, C.-C. Organometallics 2002, 21, 2066-2069.
16. Ko, B.-T.; Wu, C.-C.; Lin, C.-C. Organometallics 2000, 19, 1864-1869.
17. Campbell, E. J.; Zhou, H.; Nguyen, S. T. Org. Lett. 2001, 3, 2391-2393.
18. Brunel, J. M. Chem. Rev. 2005, 105, 857-897.
19. Campbell, E. J.; Zhou, H.; Nguyen, S. T. Angew. Chem., Int. Ed. 2002, 41, 1020-1022.
20. Doering, W. v. E.; Aschner, T. C. J. Am. Chem. Soc. 1953, 75, 393-397.
21. Shiner, V. J., Jr.; Whittaker, D. J. Am. Chem. Soc. 1963, 85, 2337-2338.
22. Shiner, V. J., Jr.; Whittaker, D. J. Am. Chem. Soc. 1969, 91, 394-398.
23. Yager, B. J.; Hancock, C. K. J. Org. Chem. 1965, 30, 1174-1179.
24. Hach, V. J. Org. Chem. 1973, 38, 293-299.
25. Cohen, R.; Graves, C. R.; Nguyen, S. T.; Martin, J. M. L.; Ratner, M. A. J. Am. Chem. Soc. 2004, 126, 14796-14803.
26. 3).
27. This dimeric aluminum complex is similar in bonding structure to those reported by the Lin group (see refs 15 and 16).
28. Kriz, O.; Casensky, B.; Lycka, A.; Fusek, J.; Hermanek, S. J. Magn. Reson. 1984, 60, 375-381.
29. Akitt, J. W. Prog. Nucl. Magn. Reson. Spectrosc. 1989, 21, 1-149.
30. Velez, K.; Quinson, J. F.; Fenet, B. J. Sol-Gel Sci. Technol. 1999, 16, 201-208.
31. 28,29
32. For this kinetic study, the initial rate of reaction was determined by GC analysis of aliquots taken from the reaction mixture at the appropriate time. Rate constants were determined from a plot of product yield versus time up to 20% yield.
33. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. 1995, 34, 1059-1070.
34. Atkins, P. W. Physical Chemistry, 6th ed.; W. H. Freeman and Company: New York, 1998; p 766.
35. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley and Sons, Inc.: New York, 1994; p 1267.
36. The slight deviation from linearity observed at higher substrate concentrations is presumably due to reaction conditions that are no longer strictly pseudo first-order (ca. only 6-fold excess of 2-propanol).
37. For recent examples of Oppenauer oxidation protocols see: (a) Ooi, T.; Otsuka, H.; Miura, T.; Ichikawa, H.; Maruoka, K. Org. Lett. 2002, 4, 2669-2672.
38. (b) Graves, C. R.; Zeng, B.-S.; Nguyen, S. T. J. Am. Chem. Soc. 2006, 128, 12596-12597.
39. Adkins, H.; Cox, F. W. J. Am. Chem. Soc. 1938, 60, 1151-1159.
40. Adkins, H.; Elofson, R. M.; Rossow, A. G.; Robinson, C. C. J. Am. Chem. Soc. 1949, 71, 3622-3629.
41. Cox, F. W.; Adkins, H. J. Am. Chem. Soc. 1939, 61, 3364-3370.
42. Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319-6337.
43. Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1997, 8, 3125-3130.
44. 3/2-propanol combination, and that these higher coordination intermediates resulted in inferior asymmetric catalysts.
45. 27Al NMR spectra, further supporting this hypothesis.
46. King, S. A.; Thompson, A.; S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689-6691.
47. Mashima, K.; Kusano, K.-H.; Sate; Matsumura, Y.-I.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3063-3076.
48. Graves, C. R.; Scheidt, K. A.; Nguyen, S. T. Org. Lett. 2006, 8, 1229-1232.