Asymmetric ring opening of meso-epoxides catalyzed by the chiral phosphine oxide BINAPO

Tetrahedron Asymmetry

Volumn 16, Issue 14, 2005, Pages 2391-2392

  Tokuoka, Eisuke ^a   Kotani, Shunsuke ^a   Matsunaga, Hirofumi ^a   Ishizuka, Tadao ^a   Hashimoto, Shunichi ^b   Nakajima, Makoto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROHYDRIN DERIVATIVE; EPOXIDE; ETHYLAMINE; PHOSPHINE OXIDE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RING OPENING;

EID: 23044454255     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.06.021     Document Type: Article

References (27)

1. P.I. Dalko, and L. Moisan Angew. Chem. Int. Ed. 40 2001 3726 3748
2. M. Benaglia, A. Puglisi, and F. Cozzi Chem. Rev. 103 2003 3401 3430
3. 'Special Issue: Asymmetric Organocatalysis', Acc. Chem. Res. 37 2004 487 631
4. V.V. Grushin Chem. Rev. 104 2004 1629 1662
5. Bis(phosphine oxide)-Fe complex: S. Matsukawa, H. Sugama, and T. Imamoto Tetrahedron Lett. 41 2000 6461 6465
6. Bis(phosphine oxide)-Sm complex: K. Mikami, and M. Yamaoka Tetrahedron Lett. 39 1998 4501 4504 For hybrid phosphine oxide ligand, see Ref. 2
7. C. Ogawa, M. Sugiura, and S. Kobayashi Angew. Chem., Int. Ed. 43 2004 6491 6493
8. M. Nakajima, S. Kotani, T. Ishizuka, and S. Hashimoto Tetrahedron Lett. 46 2005 157 159
9. M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto J. Am. Chem. Soc. 120 1998 6419 6420
10. M. Nakajima, M. Saito, and S. Hashimoto Chem. Pharm. Bull. 48 2000 306 307
11. M. Nakajima, M. Saito, and S. Hashimoto Tetrahedron: Asymmetry 13 2002 2449 2452
12. M. Nakajima, M. Saito, M. Uemura, and S. Hashimoto Tetrahedron Lett. 43 2002 8827 8829
13. M. Nakajima, T. Yokota, M. Saito, and S. Hashimoto Tetrahedron Lett. 45 2004 61 64
14. For a review, see: D.M. Hodgson, A.R. Gibbs, and G.P. Lee Tetrahedron 52 1996 14361 14384
15. E.N. Jacobsen Acc. Chem. Res. 33 2000 421 431
16. For recent successful approaches, see: W.A. Nugent J. Am. Chem. Soc. 114 1992 2768 2769
17. L.E. Martinez, J.L. Leighton, D.H. Carsten, and E.N. Jacobsen J. Am. Chem. Soc. 117 1995 5897 5898
18. B.M. Cole, K.D. Shimizu, C.A. Krueger, J.P.A. Harrity, M.L. Snapper, and A.H. Hoveyda Angew. Chem. Int. Ed. Engl. 35 1996 1668 1671
19. T. Iida, N. Yamamoto, H. Sasai, and M. Shibasaki J. Am. Chem. Soc. 119 1997 4783 4784
20. N. Oguni, Y. Miyagi, and K. Itoh Tetrahedron Lett. 39 1998 9023 9026
21. S.E. Denmark, P.A. Barsanti, K.-T. Wong, and R.A. Stavenger J. Org. Chem. 63 1998 2428 2429
22. B. Tao, M.M.-C. Lo, and G.C. Fu J. Am. Chem. Soc. 123 2001 353 354
23. R (1R,2R)-(-)-isomer, 22.0 min (5%); (1S,2S)-(+)-isomer, 24.0 min (95%).
24. 1.5 equiv of diisopropylethylamine was sufficient for achieving optimum chemical and optical yields. It is reasonable to assume that diisopropylethylamine traps the hydrogen chloride produced through the adventitious hydrolysis of tetrachlorosilane which reacts directly with the epoxide to form a chlorohydrin in a nonstereoselective process.
25. The use of trichloromethylsilane as a chloride ion source gave the racemic chlorohydrin in 84% yield, while chlorotrimethylsilane gave the product in 13% yield.
26. Dichloromethane was found to be the solvent of choice (propionitrile: 83% yield, 74% ee; toluene: 70% yield, 25% ee; THF: 56% yield, 90% ee). A reaction in THF gave 2-(4-chlorobutoxy)-1,2-diphenylethanol in 29% yield as a by-product.
27. Derivatives of BINAPO gave lower selectivities than BINAPO itself (p-Tol-BINAPO: 96% yield, 82% ee; m-Xyl-BINAPO: 98% yield, 30% ee).