Asymmetric dihydroxylation of olefins using cinchona alkaloids on highly ordered inorganic supports

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2325-2328

  Motorina, Irina ^a   Crudden, Cathleen M ^a  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINCHONA ALKALOID; SILICA GEL; SILICON DIOXIDE;

ARTICLE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM;

ALKENES; CINCHONA ALKALOIDS; HYDROXYLATION; SILICON DIOXIDE; STEREOISOMERISM;

EID: 0035954864     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010096h     Document Type: Article

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29. Compare refs 7a and b where an alkaloid supported at one point gives marginal enantioselectivities, whereas immobilizing the ligand at two positions gives significantly better results.
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43. Melosh, N. A.; Davidson, P.; Chmelka, B. F. J. Am. Chem. Soc. 2000, 122, 823. Feng, P.; Bu, X.; Stucky, G. D.; Pine, D. J. J. Am. Chem. Soc. 2000, 122, 994. Melosh, N. A.; Lipic, P.; Bates, F. S.; Wudl, F.; Stucky, G. D.; Fredrickson, G. H.; Chmelka, B. F. Macromolecules 1999, 32, 4332. Lu, Y.; Ganguli, R.; Drewien, C. A.; Anderson, M. T.; Brinker, C. J.; Gong, W.; Guo, Y.; Soyez, H.; Dunn, B.; Huang, M. H.; Zink, J. I. Nature 1997, 389, 364, Bruinsma, P. J.; Kim, A. Y.; Liu, J.; Baskaran, S. Chem. Mater. 1997, 9, 2507. Lin, H. P.; Cheng, Y.-R.; Mou, C.-Y. Chem. Mater. 1998, 10, 3772.
44. Hereafter referred to as SBA. prepared using the method described in ref 13 (Stucky et al.).
45. Pirkle, W. H.; Pochapsky, T. C.; Mahler, G. S.; Corey, D. E.; Reno, D. S.; Alessi, D. M. J. Org. Chem. 1986, 51, 4991 and ref 11.
46. See Supporting Information for the precise method used to synthesize the molecular sieve.
47. The pore size is determined from analysis of the TEM and analysis of nitrogen adsorption isotherms.
48. Note that for the heterogeneous ligands, the amount of catalyst used (1:1 with the ligand) is normalized based on the % loading of the alkaloid on the support.
49. The best method for recovery of Os involves the preparation of microencapsulated Os: Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229. Note that although this method is extremely valuable for the recovery of osmium, it involves the use of a homogeneous chiral ligand.
50. Note that the isolated yields (unoptimized) are sometimes lower for the supported alkaloid than those reported for the homogeneous ligand (see Table 2). This is a less accurate comparison because some of the diol may be lost upon chromatography.