Asymmetric catalysis via chiral aziridines

Acta Chemica Scandinavica

Volumn 50, Issue 4, 1996, Pages 361-368

  Tanner, David ^a,b   Harden, Adrian ^a   Johansson, Fredrik ^a,b   Wyatt, Paul ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002231249     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.50-0361     Document Type: Article

References (25)

1. Tanner, D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599.
2. Tanner, D. Pure Appl. Chem. 65 (1993) 1319.
3. Tanner, D., Andersson, P. G., Harden, A. and Somfai, P. Tetrahedron Lett. 35 (1994) 4631.
4. Andersson, P. G., Harden, A., Tanner, D. and Norrby P.-O. Chem. Eur. J. 1 (1995) 12.
5. (a) Preparation of (S,S)-stilbenediol (>98% ee): 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. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768 (b) Stereospecific conversion of chiral 1,2-diols into epoxidcs: Kolb, H. C. and Sharpless, K. B. Tetrahedron 48 (1992) 10515; Nicolaou, K. C. Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. J. Org. Chem. 50 (1985) 1440 (c) Imuta, M. and Ziffer. H. J. Org. Chem. 44 (1979) 2505 (d) For an alternative route to the epoxide, see: Read, J. and Campbell, I. G. M. J. Chem. Soc (1930) 2377.
6. (a) Preparation of (S,S)-stilbenediol (>98% ee): 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. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768 (b) Stereospecific conversion of chiral 1,2-diols into epoxidcs: Kolb, H. C. and Sharpless, K. B. Tetrahedron 48 (1992) 10515; Nicolaou, K. C. Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. J. Org. Chem. 50 (1985) 1440 (c) Imuta, M. and Ziffer. H. J. Org. Chem. 44 (1979) 2505 (d) For an alternative route to the epoxide, see: Read, J. and Campbell, I. G. M. J. Chem. Soc (1930) 2377.
7. (a) Preparation of (S,S)-stilbenediol (>98% ee): 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. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768 (b) Stereospecific conversion of chiral 1,2-diols into epoxidcs: Kolb, H. C. and Sharpless, K. B. Tetrahedron 48 (1992) 10515; Nicolaou, K. C. Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. J. Org. Chem. 50 (1985) 1440 (c) Imuta, M. and Ziffer. H. J. Org. Chem. 44 (1979) 2505 (d) For an alternative route to the epoxide, see: Read, J. and Campbell, I. G. M. J. Chem. Soc (1930) 2377.
8. (a) Preparation of (S,S)-stilbenediol (>98% ee): 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. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768 (b) Stereospecific conversion of chiral 1,2-diols into epoxidcs: Kolb, H. C. and Sharpless, K. B. Tetrahedron 48 (1992) 10515; Nicolaou, K. C. Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. J. Org. Chem. 50 (1985) 1440 (c) Imuta, M. and Ziffer. H. J. Org. Chem. 44 (1979) 2505 (d) For an alternative route to the epoxide, see: Read, J. and Campbell, I. G. M. J. Chem. Soc (1930) 2377.
9. (a) Preparation of (S,S)-stilbenediol (>98% ee): 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. and Zhang, X.-L. J. Org. Chem. 57 (1992) 2768 (b) Stereospecific conversion of chiral 1,2-diols into epoxidcs: Kolb, H. C. and Sharpless, K. B. Tetrahedron 48 (1992) 10515; Nicolaou, K. C. Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. J. Org. Chem. 50 (1985) 1440 (c) Imuta, M. and Ziffer. H. J. Org. Chem. 44 (1979) 2505 (d) For an alternative route to the epoxide, see: Read, J. and Campbell, I. G. M. J. Chem. Soc (1930) 2377.
10. (a) Nakajima, M., Tomioka, K., Iitaka, Y., Koga, K. Tetrahedron 49 (1993) 10793
11. (b) Hanessian, S., Meffre, P., Girard, M., Beaudoin, S., Sancéau, J.-Y., Bennani, Y. J. Org. Chem. 58 (1993) 1991 and refs, therein.
12. Berrisford, D. J., Bolm, C. and Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 34 (1995) 1059.
13. For a discussion and leading references, see: Becker, H., Ho, P. T., Kolb, H. C., Loren, S., Norrby, P.-O. and Sharpless, K. B. Tetrahedron Lett. 35 (1994) 7315.
14. For related examples see: (a) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul M. M. J. Am. Chem. Soc. 113 (1991) 726 (b) Lowenthal, R. E., Abiko, A. and Masamune, S. Tetrahedron Lett. 31 (1990) 6005 (c) Fritschi, H., Leutenegger, U. and Pfaltz, A. Helv. Chim. Acta. 71 (1988) 1553.
15. For related examples see: (a) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul M. M. J. Am. Chem. Soc. 113 (1991) 726 (b) Lowenthal, R. E., Abiko, A. and Masamune, S. Tetrahedron Lett. 31 (1990) 6005 (c) Fritschi, H., Leutenegger, U. and Pfaltz, A. Helv. Chim. Acta. 71 (1988) 1553.
16. For related examples see: (a) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul M. M. J. Am. Chem. Soc. 113 (1991) 726 (b) Lowenthal, R. E., Abiko, A. and Masamune, S. Tetrahedron Lett. 31 (1990) 6005 (c) Fritschi, H., Leutenegger, U. and Pfaltz, A. Helv. Chim. Acta. 71 (1988) 1553.
17. Doyle, M. P. In: Ojima, I., Ed., Catalytic Asymmetric Synthesis. VCH, New York 1993, Chap. 3.
18. (a) Evens, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc 116 (1994) 2742
19. (b) For a catalytic asymmetric version of this reaction, see: Evans, D. A., Faul, M. M., Bilodeau, M. T. Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328.
20. Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am. Chem. Soc. 117 (1995) 5889.
21. Andersson, P. G. and Tanner, D. Manuscript in preparation.
22. Auburn, P. R., Mackenzie, P. B. and Bosnich, B. J. Am. Chem. Soc. 107 (1985) 2033.
23. Denmark, S. E., Nakajima, N. and Nicaise, O. J.-C. J. Am. Chem. Soc. 116 (1994) 8797.
24. Lohray, B. B. and Ahuja, J. R. J. Chem. Soc. Chem. Commun. (1991) 95.
25. See, e.g., Tanner, D. and He, H. M. Tetrahedron 48 (1992) 6079.