Catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and amides by lanthanide-BINOL complexes

Tetrahedron

Volumn 59, Issue 52, 2003, Pages 10485-10497

  Ohshima, Takashi ^a   Nemoto, Tetsuhiro ^a   Tosaki, Shin Ya ^a   Kakei, Hiroyuki ^a   Gnanadesikan, Vijay ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric catalysis; Epoxidation; Lanthanide; Molecular orbital calculation

Indexed keywords

1 (1 OXO 2,6 OCTADIENYL) 4 PHENYL 1H IMIDAZOLE; 1 (1 OXO 3 PHENYL 2 PROPENYL) 1H BENZOIMIDAZOLE; 1 (1 OXO 3 PHENYL 2 PROPENYL) 2 PHENYL 1H IMIDAZOLE; 1 (1 OXO 5 PHENYL 2 PENTENYL 2 PENTENYL) 4 PHENYL 1H IMIDAZOLE; 1 (1 OXO 7 PHENY] 2,6 HEPTADIENYL) 4 PHENYL 1H IMIDAZOLE; 1 (1,7 DIOXO 2 OCTENYL) 4 PHENYL 1H IMIDAZOLE; 1 (3 CYCLOHEXYL 1 OXO 2 PROPENYL) 1H IMIDAZOLE; 1 [3 (4 BROMOPHENYL) 1 OXO 2 PROPENYL] 4 METHYL 1H IMIDAZOLE; 1 [3 (4 CHLOROPHENYL) 1 OXO 2 PROPENYL] 4 PHENYL 1H IMIDAZOLE; 1 [3 (4 METHOXYPHENYL) 1 OXO 2 PROPENYL] 4 PHENYL 1H IMIDAZOLE; 2 METHYL 1 (1 OXO 3 PHENYL 2 PROPENYL) 1H IMIDAZOLE; 4 METHYL 1 (1 OXO 3 PHENYL 2 PROPENYL) 1H IMIDAZOLE; ALDEHYDE DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE; LANTHANIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHIRALITY; DENSITY; ENANTIOSELECTIVITY; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

EID: 0347419458     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.06.010     Document Type: Article

References (52)

1. For recent reviews, see: (a) Porter M.J., Skidmore J. Chem. Commun. 2000;1215 (b) Nemoto T., Ohshima T., Shibasaki M. J. Synth. Org. Chem. Jpn. 60:2002;94.
2. For recent reviews, see: (a) Porter M.J., Skidmore J. Chem. Commun. 2000;1215 (b) Nemoto T., Ohshima T., Shibasaki M. J. Synth. Org. Chem. Jpn. 60:2002;94.
3. For recent examples, see: (a) Corey E.J., Zhang F.-Y. Org. Lett. 1:1999;1287 (b) Carde L., Davies H., Geller T.P., Roberts S.M. Tetrahedron Lett. 40:1999;5421 (c) Nemoto T., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;9569.
4. For recent examples, see: (a) Corey E.J., Zhang F.-Y. Org. Lett. 1:1999;1287 (b) Carde L., Davies H., Geller T.P., Roberts S.M. Tetrahedron Lett. 40:1999;5421 (c) Nemoto T., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;9569.
5. For recent examples, see: (a) Corey E.J., Zhang F.-Y. Org. Lett. 1:1999;1287 (b) Carde L., Davies H., Geller T.P., Roberts S.M. Tetrahedron Lett. 40:1999;5421 (c) Nemoto T., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;9569.
6. Juliá S., Masana J., Vega J.C. Angew. Chem., Int. Ed. Engl. 19:1980;929.
7. (a) Bougauchi M., Watanabe S., Arai T., Sasai H., Shibasaki M. J. Am. Chem. Soc. 119:1997;2329.
8. (b) Watanabe S., Kobayashi Y., Arai T., Sasai H., Bougauchi M., Shibasaki M. Tetrahedron Lett. 39:1998;7353
9. (c) Watanabe S., Arai T., Sasai H., Bougauchi M., Shibasaki M. J. Org. Chem. 63:1998;8090
10. (d) Nemoto T., Ohshima T., Yamaguchi K., Shibasaki M. J. Am. Chem. Soc. 123:2001;2725.
11. (a) Daikai K., Kamaura M., Inanaga J. Tetrahedron Lett. 39:1998;7321.
12. (b) Daikai K., Hayano T., Kino R., Furuno H., Kagawa T., Inanaga J. Chirality. 15:2003;83.
13. Jacobsen E.N., Deng L., Furukawa Y., Martínez L.E. Tetrahedron. 50:1994;4323.
14. (a) Armstrong A., Hayter B.R. Chem. Commun. 1998;621
15. (b) Wang Z.X., Miller S.M., Anderson O.P., Shi Y. J. Org. Chem. 64:1999;6443
16. (c) Solladié-Cavallo A., Bouérat L. Org. Lett. 2:2000;3531.
17. (d) Wu X.-Y., She X., Shi Y. J. Am. Chem. Soc. 124:2002;8792.
18. Weitz E., Scheffer A. Ber. Dtsch. Chem. Ges. 54:1921;2327.
19. (a) Nemoto T., Ohshima T., Shibasaki M. J. Am. Chem. Soc. 123:2001;9474
20. (b) Nemoto T., Tosaki S.-., Ohshima T., Shibasaki M. Chirality. 15:2003;306.
21. (a) Nemoto T., Kakei H., Gnanadesikan V., Tosaki S.-., Ohshima T., Shibasaki M. J. Am. Chem. Soc. 124:2002;14544
22. (b) Tosaki S.-., Nemoto T., Ohshima T., Shibasaki M. Org. Lett. 5:2003;495.
23. For a review, see: Ager D.J., Prakash I., Schaad D.R. Aldrichchim. Acta. 30:1997;3.
24. AM1 calculations were performed with the MOPAC version 6.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Tomasi, J.; Farkas, O.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Calculations were performed with the Gaussian 98 program package; Revision A.7, Gaussian, Inc., Pittsburgh PA, 1998.
26. (a) Becke A.D. J. Chem. Phys. 98:1993;5648
27. (b) Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785.
28. For an example, see: Page P.C.B., Gareh M.T., Porter R.A. Tetrahedron Lett. 34:1993;5159. and references therein.
29. For recent examples, see: (a) Furutani T., Imashiro R., Hatsuda M., Seki M. J. Org. Chem. 67:2002;4599 (b) Imashiro R., Kuroda T. J. Org. Chem. 68:2003;974. and references therein.
30. For recent examples, see: (a) Furutani T., Imashiro R., Hatsuda M., Seki M. J. Org. Chem. 67:2002;4599 (b) Imashiro R., Kuroda T. J. Org. Chem. 68:2003;974. and references therein.
31. Asymmetric synthesis of α,β-epoxy amides using a highly enantioselective Darzens reaction of a camphor-derived sulfonium amide was reported, see: Aggarwal V.K., Hynd G., Picoul W., Vasse J.-L. J. Am. Chem. Soc. 124:2002;9964.
32. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
33. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
34. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
35. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
36. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
37. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
38. For recent examples of tandem catalytic processes, see: (a) Jeong N., Seo S.-D., Shin J.-Y. J. Am. Chem. Soc. 122:2000;10220 (b) Yamasaki S., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;1256 (c) Evans P.A., Robinson J.E. J. Am. Chem. Soc. 123:2001;4609 (d) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (e) Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. Angew. Chem., Int. Ed. 40:2001;4620 (f) Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., Umani-Ronchi A. J. Org. Chem. 67:2002;3700 (g) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636.
39. 3AsO retarded the epoxide opening reaction.
40. Reagents for the first epoxidation successfully prevented the formation of by-products. For the details, see Ref. 9a.
41. (a) Grimmelikhuijzen C.J.P., Rinehart K.L., Jacob E., Graff D., Reinscheid H.-P., Staley A.L. Proc. Natl. Acad. Sci., USA. 87:1990;5410
42. (b) Ishida K., Okita Y., Matsuda H., Okino T., Murakami M. Tetrahedron. 55:1999;10971.
43. Speranza G., Morelli C.F., Manitto P. Synthesis. 2000;123.
44. Orita A., Nagano Y., Hirano J., Otera J. Synlett. 2001;637.
45. He L., Byun H.-S., Bittman R. Tetrahedron Lett. 39:1998;2071.
46. Calis I., Kuruüzüm A., Demirezer L.O., Sticher O., Ganci W. J. Nat. Prod. 62:1999;1101.
47. For the detailed data, see the Supporting Information of Ref. 9b.
48. Rychnovsky S.D., Griesgraber G. J. Org. Chem. 57:1992;1559.
49. Behrens C.H., Sharpless K.B. J. Org. Chem. 50:1985;5696.
50. Meth-Cohn O., Moore C., Taljaard H.C. J. Chem. Soc., Perkin Trans. 1. 1988;2663.
51. Kuwano R., Takahashi M., Ito Y. Tetrahedron Lett. 39:1998;1017.
52. For the detailed data, see the Supporting Information of Ref. 10a.