Asymmetric desymmetrization of a pseudo-meso endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one by chiral amines

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8003-8006

  Bakkeren, Frank J A D ^a   Ramesh, Namakkal G ^a   De Groot, Debby ^a   Klunder, Antonius J H ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CUBANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030605163     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01810-2     Document Type: Article

References (23)

1. 1. Zhu, J.; Yang, J.Y.; Klunder, A.J.H.; Liu, Z.Y.; Zwanenburg, B. Tetrahedron, 1995, 51, 5847, and references cited therein.
2. 2. (a) Garland, R.B.; Miyano, M.; Pireh, D.; Clare, M.; Finnegan, P.M.; Swenton, L. J. Org. Chem., 1990, 55, 5854.
3. (b) Liu, Z.-Y.; He, L.; Zheng, H. Synlett, 1993, 191.
4. (c) Ogasawara, K. Pure Appl. Chem., 1994, 66, 2119.
5. 3. (a) Zwanenburg, B.; Klunder, A.J.H. Strained Cage Systems; Synthetic and Structural Implications. In Strain and Its Implications in Organic Chemistry; De Meijere, A.; S. Blechert Eds.; Kluwer Academic Publishers: Amsterdam, 1989; 405, and references cited therein,
6. (b) Dilling, W.L. Recent Advances in Selected Aspects of Bishomocubane Chemistry. In Carbocyclic Cage Compounds: Chemistry and Applications; Osawa, E.; Yonemitsu, O. Eds.; New York: VCH Publishers, 1992; 249.
7. (c) Marchand, A.P., Chem. Rev., 1989, 89, 1011.
8. (d) Ogino, T.; Wada, F.; Kaneko, S. Tetrahedron Lett., 1995, 36, 6523.
9. 4. Klunder, A.J.H.; Huizinga, W.B.; Hulshof, A.J.M.; Zwanenburg, B. ibid., 1986, 27, 2543.
10. 5. (a) Takano, S.; Moriya, M.; Tanaka, K.; Ogasawara, K. Synthesis, 1994, 687.
11. (b) Tanaka, K.; Ogasawara, K. ibid. 1995, 1237.
12. 6. In addition a stereoselective enzymatic esterification of a meso-tricyclodecadiene-1,3-diol has been reported7. However, this approach seems less practical than the resolution of alcohol 3 as it involves two more steps starting from 3 and allows the formation of only one of the possible antipodes of 1.
13. 7. Liu, Z.-Y.; Zheng, H. Tetrahedron: Asymm., 1993, 4, 2277.
14. 8. Dols, P.P.M.A.; Klunder, A.J.H.; Zwanenburg, B. Tetrahedron, 1994, 50, 8515.
15. 9. DePuy, C.H.; Zaweski, E.F. J. Am. Chem. Soc., 1959, 81, 4920.
16. 10. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc., 1995, 68, 36.
17. 11. (a) Faber, K. Biotransformations in Organic Chemistry; Heidelberg: Springer Verlag, 1992.
18. (b) Drauz, K.; Waldmann, H. (Eds.) Enzyme Catalysis in Organic Synthesis, Vol. I and II; New York: VCH Publishers, 1995.
19. 12. Gelder, R. de; Smits, J.M.M.; Bakkeren, F.J.A.D.; Ramesh, N.G.; Klunder, A.J.H. X-Ray crystallographic data will be published elsewhere.
20. 13. (a) Greenhill, J.V. Chem. Soc. Rev., 1977, 6, 277, and references cited therein.
21. (b) Miftakhov, M.S.; Khalikov, R.M.; Akhmetvaleev, R.R.; Tolstikov, G.A. Russ. J. Org. Chem. (Engl. Transl.), 1995, 31, 182.
22. (c) Edafiogho, I.O.; Moore, J.A.; Alexander, M.S.; Scott, K.R. J. Pharm. Sci., 1994, 83, 1155.
23. (d) Naringrekar, V.H.; Stella, V.J. J. Pharm. Sci., 1990, 79, 138.