Ligand-dependent reversal of facial selectivity in the asymmetric dihydroxylation

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7978-7979

  Vanhessche, Koen P M ^a,b   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Analysis and Perception Department   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000758569     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961189t     Document Type: Article

References (20)

1. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
2. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
3. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
4. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
5. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
6. A [3 + 2] mechanism was originally proposed by Böseken for reactions of permanganate and adopted by Criegee for osmium tetraoxide: (a) Böseken, J. Recl. Trav. Chim. 1922, 41, 199. For the [2 + 2] mechanism, see: (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213. (d) Gable, K. P.; Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955. (e) Gable, K. P.; Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
7. (a) Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 118, 1278.
8. (b) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35.
9. (c) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319 and references cited therein.
10. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
11. Becker, H.; King, S. B.; Taniguchi, M.; Vanhessche, K. P. M.; Sharpless, K. B. J. Org. Chem. 1995, 60, 3940.
12. A general procedure for the AD of α-alkylstyrenes is given in the Supporting Information.
13. Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375.
14. Related reversals of enantiofacial selectivity have also been observed for α-arylstyrenes; Loren, S.; Sharpless, K. B. unpublished results.
15. Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu., D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
16. We have also been able to rationalize the trends in facial selectivity for α-alkylstyrenes using molecular mechanics calculations (see ref 3b for parameters). This approach is of course much more complicated than the simple "binding pocket" mnemonic, but it is especially informative for the exceptional cases 8 and 16 in Table 1: Becker, H.; Loren, S.; Vanhessche, K.; Sharpless, K. B. Unpublished results.
17. Vanhessche, K.; Sharpless, K. B. Chem, Eur. J., in press.
18. -1)-indicate slightly lower "in-close" steric demands for the 1-adamantyl substituent. If these small calculated differences are real, it is interesting to speculate on the origin of the effect. The adamantane structure is rigid and compact, and significant bond angle variations are impossible. If one now imagines the creation of the tert-butyl group by formal hydrogenolysis of the three appropriate C-C bonds in adamantane, what remains, in place of the very polycyclic framework that made deformations a nonissue, are three new C-H bonds, one on each of the methyls of what is now a tert-butyl group. Hence, cyclic constraint has in a sense been exchanged for nonbonded repulsion in the acyclic analog, and even a very slight spreading of the methyls (angle bending) could account for the tert-butyl group's larger size apparent.
19. Manoharan, M.; Eliel, E. L. Tetrahedron Lett. 1984, 25, 3267.
20. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.