Toward an understanding of the high enantioselectivity in the osmium-catalyzed asymmetric dihydroxylation. 3. New insights into isomeric forms of the putative osmaoxetane intermediate

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 35-41

  Norrby, Per Ola ^a   Becker, Heinrich ^b   Sharples, K Barry ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003084653     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952470c     Document Type: Article

References (57)

1. ΔG‡ is usually between 5 and 7 kcal/mol. (a) Kwong, H.-L. Ph.D. Thesis, Massachusetts Institute of Technology, 1993. (b) Nelson, D W ; Sharpless, K. B. Unpublished results.
2. ΔG‡ is usually between 5 and 7 kcal/mol. (a) Kwong, H.-L. Ph.D. Thesis, Massachusetts Institute of Technology, 1993. (b) Nelson, D W ; Sharpless, K. B. Unpublished results.
3. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L., Morikawa, K ; Wang, Z.-M.; Xu, D.; Zhang, X.-L J. Org, Chem. 1992, 57, 2768 and references cited therein.
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38. Norrby, P.-O.; Gable, K. P. J. Chem. Soc., Perkm Trans. 2, in press
39. Puckering is proposed to play a key role in the extrusion of alkenes from rhenium(V) diolates. which is essentially the microscopic reverse of the osmylation process: (a) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc 1995, 117, 955. (b) Gable, K. P. Personal communication.
40. Puckering is proposed to play a key role in the extrusion of alkenes from rhenium(V) diolates. which is essentially the microscopic reverse of the osmylation process: (a) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc 1995, 117, 955. (b) Gable, K. P. Personal communication.
41. (a) Footnote 3 in: Sharpless, K. B.; Akashi, K. J. Am. Chem Soc. 1976, 98, 1986.
42. (b) Shing, T. K. M.; Tai, V. W.-F., Tam, E. K W Angw. Chem., Int. Ed. Engl. 1994, 33, 2312.
43. Xu, D.; Sharpless, K. B. Unpublished results.
44. Isodesmic comparions are expected to give reliable results even at fairly low levels of theory: Hehre. W. J.; Radom. L.; Schleyer, P. v. R.; Pople. J. A., Ab Initio Molecular Orbital Theory; Wiley. New York. 1986
45. Andersson, P G.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7047.
46. Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278.
47. Vanhessche, K P. M.; Sharpless. K. B. Unpublished results. See also ref 2f.
48. Since 1987 a number of cinchona derivatives have been used, but for most of these ligands where a comparison has been made, the results for the methylstyrenes show, similar trends; see ref 2.
49. Kwong, H.-L.; Sorato, C.; Ogino, Y ; Chen, H.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 2999.
50. Wang, L.; Sharpless. K B. Unpublished results.
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52. 2-PHAL than by DHQD-CLB (see ref 16).
53. Dijkstra, G. D. H.; Kellog, R. M.; Wynberg, H.; Svendsen, J. S.; Markó, I.; Sharpless, K. B. J Am. Chem. Soc. 1989, 111, 8069.
54. DGauss 1.1.1, part of UniChem 1.1.1 from Cray Research. Inc.
55. Becker, H ; Soler. M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345.
56. (a) Hesse, O. Justus Liebigs Ann. Chem. 1887, 241, 255.
57. (b) Hesse, O. Justus Liebigs Ann. Chem. 1882, 214, 1.