Transformation of a Racemic Mixture by a Chiral Reagent or Catalyst to Give Regioisomeric Products

Croatica Chemica Acta

Volumn 69, Issue 2, 1996, Pages 669-680

  Kagan, Henri B ^a  

^a Univ des Sciences Paris Sud   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000679847     PISSN: 00111643     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, and K. B. Sharpless, J. Am. Chem. Soc. 103 (1981) 6237-6240.
2. M. S. Van Nieuwenhze and K. B. Sharpless, J. Am. Chem. Soc. 115 (1993) 7864-7865.
3. S. El Baba, J.-C. Poulin, and H. B. Kagan, Tetrahedron 40 (1984) 4275-4284.
4. J. P. Guetté and A. Horeau, Bull. Soc. Chim. Fr. (1967) 1747-1752.
5. H. B. Kagan, and J.-C. Fiaud, Topics in Stereochem. 18 (1988) 249-330.
6. C. Bolm, G. Schlingloff, and K. Weickhardt, Angew. Chem., Int. Ed. Engl. 33 (1994) 1848-1849.
7. C. Bolm, and G. Schlingloff, J. Chem. Soc., Chem. Commun (1995) 1247-1248.
8. H. D. Kim, H. Kawasaki, M. Nakajima, and K. Koga, Tetrahedron: Asymmetry 1 (1990) 295-298.
9. 0)/2.
10. R. Azerad, Bull. Soc. Chim. Fr. 132 (1995) 17-51.
11. F. Petit and R. Furstoss, Tetrahedron: Asymmetry 4 (1993) 1341-1352.
12. V. Alphand and R. Furstoss, J. Org. Chem. 57 (1992) 1306-1309.
13. B. Adger, M. T. Bes, G. Grogan, R. McCaque, S. Pedragosa-Moreau, S. M Roberts, R. Villa, P. W. H. Wan, and A. J. Willetts, J. Chem. Soc., Chem. Commun. (1995) 1563-1564.
14. A. Gusso, C. Baccin, F. Pinna, and G. Strukul, Organometallics 13 (1994) 3442-3451.
15. E. E. Eliel, S. H. Wylen, and L. N. Mander (Eds.), Stereochemistry of Organic Compounds, J. Wiley and Sons, New York, 1994, p. 2208.
16. T. Honda, N. Sano, and K. Kanai, Heterocycles 41 (1995) 425-429.
17. Z. C. Yang and W. S. Zhou, Tetrahedron Letters 36 (1995) 5617-5618.
18. Z. C. Yang, X. B. Jiang, Z. M. Wang, and W. S. Zhou, J. Chem. Soc., Chem. Commun. (1995) 2389-2390.
19. Transformations in Ref. 18 (one example in Scheme 7) are called by the authors »a highly efficient kinetic resolution« because of the high ee's of the two isomeric epoxides. The starting bisallylic alcohols could not be recovered because they were destroyed in the work-up. Considering the data of Scheme 7 and the discussion in the conclusion, it is obvious that there was no kinetic resolution but a high »chiral regioselective control«.
20. A special case is the recently described intramolecular cyclopropanation of racemic allylic diazoacetates catalyzed by chiral rhodium complexes. There were strong divergent enantiomer differences, one enantiomer gave intramolecular cyclopropanation while the other enantiomer was transformed through hydride abstraction / elimination into two achiral compounds.
21. M. P. Doyle, A. B. Dyatkin, A. V. Kalinin, and D. A. Ruppar, J. Am. Chem. Soc. 117 (1995) 11021-11022.