Epoxidation of p-methoxycinnamates using chiral dioxiranes derived from new trisubstituted halogenated cyclohexanones: Enhanced efficiency of ketones having an axial halogen

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3531-3534

  Solladie Cavallo A ^a   Bouerat L ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041327113     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0001721     Document Type: Article

References (17)

1. (a) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492.
2. (b) Wang, Z. X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328-2329.
3. (c) Tu, Y.; Wang, Z. X.; Shi, Y. J Am. Chem. So 1996, 118, 9806-9807. For further information, see the following review:
4. (d) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859.
5. (a) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288-8289.
6. (b) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621-622.
7. Wang, Z. X.; Miller, S. M.; Anderson, O. P.; Shi, Y. J. Org. Chem. 1999, 64, 6443-6458.
8. Solladié-Cavallo, A.; Bouérat, L. Tetrahedron: Asymmetry 2000, 11, 935-941. Ketone 4a has already been prepared and tested to study effects of remote substituents on catalytic asymmetric epoxidation. Cf. Yang D.; Yip Y. C.; Chen J.; Cheung K. K. J. Am. Chem. Soc. 1998, 120, 7659-7660.
9. Solladié-Cavallo, A.; Bouérat, L. Tetrahedron: Asymmetry 2000, 11, 935-941. Ketone 4a has already been prepared and tested to study effects of remote substituents on catalytic asymmetric epoxidation. Cf. Yang D.; Yip Y. C.; Chen J.; Cheung K. K. J. Am. Chem. Soc. 1998, 120, 7659-7660.
10. 4, and analyzed.
11. 3).
12. Mobile phase: iPrOH/hexane (10/90) for Chiralcel OG and iPrOH/ hexane (25/75) for Chiralcel OD. Flow rate: 1 mL/min.
13. Armstrong A.; Washington I.; Houk K. N. J. Am. Chem. Soc. 2000, 122, 6297-6298.
14. -1.
15. Following procedure B at 0°C and without ketone, no epoxidation was observed.
16. For assignment of the (2R,3S)-configuration to (-)-7a, cf. Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. For assignment of (-)-7b, cf. ref 6.
17. For assignment of the (S,S)-configuration to the (-)-stilbene oxide, cf. Imuta, M.; Ziffer, H. J. Org. Chem. 1979, 44, 2505-2509.