Catalytic and highly enantioselective aziridination of styrene derivatives

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9245-9248

  Nishikori, Hisashi ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MANGANESE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

EID: 0030590954     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02195-8     Document Type: Article

References (14)

1. 1. Padwa, A.; Woolhouse, A. D. In "Comprehensive Heterocyclic Chemistry," Ed. by Lwowski, W. Pergamon, Oxford, 1984; Vol. 7, pp47-93.
2. 2. a) Evans, D. A.; Woepel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728.
3. b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. ibid. 1993, 115, 5328-5329.
4. c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373-7376.
5. 3. Li, Z.; Conse, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
6. 4. Tanner, D.; Andersson, P. G.; Harden, A.; Somfari, P. Tetrahedron Lett. 1994, 35, 4631-4634.
7. 5. Noda, K.; Hosoya, R; Irie, R.; Ito, Y.; Katsuki, K. Synlett 1993, 469-471.
8. 6. Although Masamune and coworker reported that Cu(I)-bisoxazoline complex catalyzed aziridination of styrene with high enantioselectivity of 88% ee (reference 2c), Evans and coworkers have insisted that such a high enantioselectivity was not reproduced in the reaction using the same Cu(I)-bisoxazoline complex as a catalyst (reference 2b).
9. 7. a) Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827-11838.
10. b) Katsuki, T. J. Synth. Org. Chem. Jpn. 1995, 55, 940-951.
11. 8. For the review on ligand acceleration, see: Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
12. 9. Enantiomeric excess of the product was determined by HPLC analysis using Daicel Chiralcel OJ (hexane:i-PrOH = 1:1).
13. 10. Complex 1 bearing (2S,3S)-2,3-diaminobutane as its ethylenediamine moiety showed higher asymmetric induction than the corresponding complex bearing (1S,2S)-1,2-diphenylethylenediamine instead (reference 3).
14. 11. Modification of the ethylenediamine moiety of the early (salen)manganese complexes affected their catalytic activity to a small extent (reference 5).