Oxidative asymmetrization of racemic alkenes: Asymmetric synthesis of optically active dicyclopentadiene derivatives

Synlett

Volumn , Issue 8, 1999, Pages 1231-1234

  Kohmura, Yoshinori ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Allylic oxidation; Chiral copper(II) complex; Oxidative asymmetrization; Tris(oxazoline) ligand

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; OXIDATION; RACEMIC MIXTURE; SYNTHESIS;

EID: 0032791793     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2821     Document Type: Article

References (24)

1. Newman, P. "Optical Resolution Procedures for Chemical Compounds", Optical Resolution Information Center, Manhattan College, New York, (1978).
2. For the review of kinetic resolution, see: Kagan, H. B.; Fiaud, J. C. Topics Stereochem. 1988, 18, 249.
3. For the review of transition metal-catalyzed asymmetric allylic substitution, see: a) Hayashi, T. In "Catalytic Asymmetric Synthesis" ed by Ojima, I. VCH publishers, Inc., New York, (1993), pp 325.
4. b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
5. c.)Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689.
6. a) Kharasch, M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80, 756.
7. b) Kharasch, M. S.; Fono, A. J. Org. Chem. 1958, 23, 324.
8. c.)For the review of oxidation using a combination of copper complex and peroxyester, see: Rawlinson, D. J.; Sosnovsky, G. Synthesis 1972, 1.
9. a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831.
10. b) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945.
11. c.)Andrus, M. B.; Chen, X. Tetrahedron 1997, 53, 16229.
12. d.)Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961.
13. a) Kawasaki, K.; Tsumura, S.; Katsuki, T. Synlett 1995, 1245.
14. b) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337.
15. 4 and ii) protection of the corresponding diol. The configuration of the intermediary diol was determined to be exo by comparing its NMR data with the authentic sample prepared by the reported procedure (reference 13).
16. For the review on the use of chiral dicyclopentadienes in organic synthesis, see: a) Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119.
17. b) Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 29.
18. The relative configurations of 7 and 8 were unambiguously confirmed by their X-ray analyses but absolute configurations are unknown.
19. Olefins are known to coordinate to cationic copper ion: a) Quan, R.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156.
20. b) Lo, M. M.-C.; Fu. G. C. J. Am. Chem. Soc. 1998, 120, 10270.
21. The configuration of 11 was determined as drawn by comparing NMR data and the specific optical rotation with the authentic samples prepared by the reported procedure (reference 14) after its hydrolysis.
22. 4 and ii) the protection of diol as an acetonide.
23. Ogino, T.; Mochizuki, K. Chem. Lett. 1979, 443.
24. Takano, S.; Moriya, M.; Tanaka, K.; Ogasawara, K. Synthesis 1994, 687.