Highly enantioselective epoxidation of trans-stilbenes catalyzed by chiral ketones

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 11311-11312

  Yang, Dan ^a   Wang, Xue Chao ^a   Wong, Man Kin ^a   Yip, Yiu Chung ^a   Tang, Man Wai ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; STILBENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029923940     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626805     Document Type: Article

References (20)

1. For recent reviews on catalytic asymmetric epoxidation of unfunctionalized olefins, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2.
2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404.
3. (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991,113,7063.
4. (b) Lee, N. H.; Muci, A. R.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 5055.
5. Deng, L.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320.
6. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457.
7. (e) Irie, R.; Noda, K.; Ito, Y.; Katsuki, T. Tetrahedron Lett. 1991, 32, 1055.
8. (f) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311.
9. (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378.
10. (b) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197.
11. Brandes, B. D.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5123.
12. (a) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333.
13. (b) Naruta, Y.; Ishihara, N.; Tani, F.; Maruyama, K. Bull. Chem. Soc. Jpn. 1993, 66, 158.
14. In the X-ray structure of ketone 1, the distance between H-3 or H-3′ and the keto group is ca. 5 Å, approximately the length of a phenyl ring.
15. The structure of chiral dioxirane (R)-1a was created using the Chem 3D program on the basis of the coordinates from the X-ray structure of ketone 1.
16. 2 symmetric chiral element was changed from 1,1′-binaphthyl-2,2′-dicarboxylic acid to 6,6′-dinitro-2,2′-diphenic acid, similar ee values were observed. Unpublished results.
17. 13C NMR, IR, HRMS, and LRMS (see Supporting information).
18. Baumstark et al. proposed a spiro TS rather than a planar TS for dioxirane epoxidation on the basis of the observation that certain cis-dialkyl alkenes were ca. 7-10 times more reactive than their jrani-isomers. However, for phenyl-substituted alkenes, certain frans-isomers were slightly more reactive than cis-isomers.
19. Stereoviews of the favored and disfavored orientations for both spiro TS and planar TS are provided as Supporting Information.
20. Although giving similar enantioselectivities, ketones (R)-2 and (R)-3 were less reactive than (R)-7 at 0 °C.