What is the origin of highly asymmetric induction by a chiral (salen)manganese(III) complex? Design of a conformationally fixed complex and its application to asymmetric epoxidation of 2,2-dimethylchromenes

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4325-4328

  Ito, Yoshio N ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENE DERIVATIVE; MANGANESE DERIVATIVE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG DESIGN; DRUG SYNTHESIS; EPOXIDATION;

EID: 0032508082     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00763-1     Document Type: Article

References (19)

1. 1) Katsuki, T. J. Mol. Catalyst A, 1996, 113, 87-107.
2. 2) Kokubo, C.; Katsuki, T. Tetrahedron, 1997, 52, 13895-13900, and references cited therein.
3. 3) Miyafuji, A.; Katsuki, T. Synlett, 1997, 836-838.
4. 4) Katsuki, T. Coord. Chem. Rev., 1995, 140, 189. Katsuki, T. J. Synth. Org. Chem. Jpn., 1995, 53, 940. Jacobsen, E. N. In "Catalytic Asymmetric Synthesis" ed by I. Ojima, VCH publishers, Inc., New York (1993), pp. 159-202.
5. 4) Katsuki, T. Coord. Chem. Rev., 1995, 140, 189. Katsuki, T. J. Synth. Org. Chem. Jpn., 1995, 53, 940. Jacobsen, E. N. In "Catalytic Asymmetric Synthesis" ed by I. Ojima, VCH publishers, Inc., New York (1993), pp. 159-202.
6. 4) Katsuki, T. Coord. Chem. Rev., 1995, 140, 189. Katsuki, T. J. Synth. Org. Chem. Jpn., 1995, 53, 940. Jacobsen, E. N. In "Catalytic Asymmetric Synthesis" ed by I. Ojima, VCH publishers, Inc., New York (1993), pp. 159-202.
7. 5) Hamada, T.; Fukuda, T.; Imanishi, H; Katsuki, T. Tetrahedron, 1996, 52, 515-530. Noguchi, Y.; Irie, R.; Fukuda, T.; Katsuki, T. Tetrahedron Lett., 1996, 37, 4533-4536.
8. 5) Hamada, T.; Fukuda, T.; Imanishi, H; Katsuki, T. Tetrahedron, 1996, 52, 515-530. Noguchi, Y.; Irie, R.; Fukuda, T.; Katsuki, T. Tetrahedron Lett., 1996, 37, 4533-4536.
9. 6) Hashihayata, T.; Ito, Y; Katsuki, T. Synlett, 1996, 1079-1081. Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron, 1997, 53, 9541-9552.
10. 6) Hashihayata, T.; Ito, Y; Katsuki, T. Synlett, 1996, 1079-1081. Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron, 1997, 53, 9541-9552.
11. 7) Schwenkreis, T.; Berkessel, A. Tetrahedron Lett., 1993, 34, 4785-4788.
12. 8) Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827-11838.
13. 9) The epoxidation of 5a using a complex prepared from 3 and ethylenediamine where the carboxylate group was eliminated, produced (3S,4S)-epoxide in 92% with 37% ee.
14. 10) Sasaki, H.; Irie, R.; Katsuki, T. Synlett, 1994, 356-358. Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron, 1994, 50, 4311-4322. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827-11838.
15. 10) Sasaki, H.; Irie, R.; Katsuki, T. Synlett, 1994, 356-358. Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron, 1994, 50, 4311-4322. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827-11838.
16. 10) Sasaki, H.; Irie, R.; Katsuki, T. Synlett, 1994, 356-358. Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron, 1994, 50, 4311-4322. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827-11838.
17. 2O: H, 4.43, C, 77.19, N, 3.16%. Found: H, 4.29, C, 77.18, N, 3.11%.
18. 3).
19. 13) The results described in this paper are not compatible with the hypothesis that the salen ligands of oxospecies are planar: Palucki, M.; Finney, N. S.; Pospisil, P. J., Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 948-954.