Catalytic asymmetric epoxidation of naphthoquinone derivatives under phase-transfer catalyzed conditions

Synlett

Volumn , Issue 11, 1998, Pages 1201-1202

  Arai, Shigeru ^a   Oku, Makoto ^a   Miura, Motoko ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002975764     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1932     Document Type: Article

References (23)

1. (a) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. in press. Quite recently, we have published some successful results for PTC-catalyzed asymmetric reactions,
2. see (b) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145.
3. (c) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
4. Quite recently, a successful result that utilized O-protected chiral quaternary ammonium salt as PTC with NaOCl was reported, see (a) Lygo, B.; Wainwright, G. P. Tetrahedron Lett. 1998, 39, 1599.
5. A review for PTC catalyzed asymmetric epoxidation was published, see (b) Ebrahim, S.; Wills, M.; Tetrahedron Asymmetry 1997, 8, 3163.
6. Recently, successful results of asymmetric epoxidation promoted by metal reagents were reported, see (c) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Eng. 1996, 35, 1725.
7. (d) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329.
8. (e) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Eng. 1997, 36, 410.
9. (a) Helder, R.; Hummelen, J. C.; Laane, R. W. P. M.; Wiering, J. S.; Wynberg, H. Tetrahedron Lett. 1976, 21, 1831.
10. (b) Wynberg, H.; Marsman, B. J. Org. Chem. 1980, 45, 158.
11. (c) Pluim, H.; Wynberg, H. J. Org. Chem. 1980, 45, 2498.
12. (d) Snatzke, G.; Wynberg, H.; Feringa, B.; Marsman, B. G.; Greydanus, B.; Pluim, H. J. Org. Chem. 1980, 45, 4094.
13. (e) Harigaya, Y.; Yamaguchi, H.; Onda, M. Heterocycles 1981, 15, 183.
14. (f) Baba, N.; Oda, J. Kawaguchi, M. Agric. Biol. Chem. 1986, 50, 3113.
15. (a) Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. J. Org. Chem. 1998, 63, 3526.
16. (b) Macdonald, G.; Alcaraz, L.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 5433.
17. (a) Willingham, A. K.; Matchiner, J. T. Biochem. J. 1974, 140, 435.
18. (b) Suttie, J. W.; Lawson, A. E.; Canfield, L. M.; Carlisle, T. L. Fed. Proc. Fed. Am. Soc. Exp. Biol. 1978, 37, 2605.
19. Wynberg et al. reported that 2a was obtained via asymmetric epoxidation with 5% ee in 60-70% yield under phase-transfer catalyzed conditions, see ref. 3c,d.
20. D and CD spectral data by comparison with the literature results, see ref. 3c,d.
21. 3d
22. All PTCs used in this reaction system were easily prepared from quinidine and commercially available arylmethyl halide derivatives. PTCs having alkyl groups on the phenyl ring afforded 2 with better ee than PTCs having other electron-withdrawing or donating groups.
23. 2O = 3:1) gave the desired product 2d (201.8 mg, 93%, 70% ee) as a colorless oil. Ee was determined by HPLC analysis (DAICEL CHIRALCEL OD, hexane:i-PrOH = 50:1, flow rate = 0.5 mL/min, retention time; 12.5 min (minor) and 13.0 min (major)).