Development of a new Lewis acid-catalyzed Claisen rearrangement [3]

Journal of the American Chemical Society

Volumn 121, Issue 41, 1999, Pages 9726-9727

  Yoon, Tehshik P ^a   Dong, Vy M ^a   MacMillan, David W C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; CHLORIDE; MORPHOLINE DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; ENANTIOMER; LETTER; REACTION ANALYSIS;

EID: 0032731884     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9919884     Document Type: Letter

References (37)

1. Claisen, B. Chem. Ber. 1912, 45, 3157.
2. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
3. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
4. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
5. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
6. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
7. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
8. For recent reviews on the Claisen rearrangement, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, Chapter 7.2, p 827. (b) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847. (c) Blechert, S. Synthesis 1989, 71. (d) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (e) Moody, C. J. Adv. Hetrocycl. Chem. 1987, 42, 203. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (g) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 503.
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20. (b) Saito, S.; Shimada, K.; Yamamoto, H. Synlett 1996, 720.
21. An asymmetric catalytic variant of the Claisen rearrangement has yet to be realized. Enantioselective Clasien rearrangements involving stoichiometric chiral promoters have been documented: (a) Maruoka, K.; Susumu, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165. (b) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791. (c) Corey, E. J.; Lee, D. H. J. Am. Chem. Soc. 1991, 113, 4026. (d) Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193.
22. An asymmetric catalytic variant of the Claisen rearrangement has yet to be realized. Enantioselective Clasien rearrangements involving stoichiometric chiral promoters have been documented: (a) Maruoka, K.; Susumu, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165. (b) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791. (c) Corey, E. J.; Lee, D. H. J. Am. Chem. Soc. 1991, 113, 4026. (d) Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193.
23. An asymmetric catalytic variant of the Claisen rearrangement has yet to be realized. Enantioselective Clasien rearrangements involving stoichiometric chiral promoters have been documented: (a) Maruoka, K.; Susumu, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165. (b) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791. (c) Corey, E. J.; Lee, D. H. J. Am. Chem. Soc. 1991, 113, 4026. (d) Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193.
24. An asymmetric catalytic variant of the Claisen rearrangement has yet to be realized. Enantioselective Clasien rearrangements involving stoichiometric chiral promoters have been documented: (a) Maruoka, K.; Susumu, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165. (b) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791. (c) Corey, E. J.; Lee, D. H. J. Am. Chem. Soc. 1991, 113, 4026. (d) Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193.
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27. (a) Edstrom, E. D. J. Am. Chem. Soc. 1991, 113, 6690.
28. (b) Ishida, M.; Muramaru, H.; Kato, S. Synthesis 1989, 562.
29. (c) Maruya, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Thomas, R. J.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1992, 1617.
30. (d) Rosini, G.; Spinetti, G. G.; Foresti, E.; Predella, G. J. Org. Chem. 1981, 46, 2228.
31. For conceptually related zwitterionic aza-Claisen rearrangements see: (a) Kunng, F.-A.; Gu, J.-M.; Chao, Y.; Mariano, P. S. J. Org. Chem. 1983, 48, 4262. (b) Diederich, M.; Nubbemeyer, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1026. (c) Deur, C. J.; Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1996, 61, 2871. See also ref 5a.
32. For conceptually related zwitterionic aza-Claisen rearrangements see: (a) Kunng, F.-A.; Gu, J.-M.; Chao, Y.; Mariano, P. S. J. Org. Chem. 1983, 48, 4262. (b) Diederich, M.; Nubbemeyer, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1026. (c) Deur, C. J.; Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1996, 61, 2871. See also ref 5a.
33. For conceptually related zwitterionic aza-Claisen rearrangements see: (a) Kunng, F.-A.; Gu, J.-M.; Chao, Y.; Mariano, P. S. J. Org. Chem. 1983, 48, 4262. (b) Diederich, M.; Nubbemeyer, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1026. (c) Deur, C. J.; Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1996, 61, 2871. See also ref 5a.
34. Tidwell, T. T. Ketenes; Wiley: New York, 1995.
35. Staudinger, H. Chem. Ber. 1905, 38, 1735.
36. Preliminary studies indicate pyrrolidine- and dimethylamine-derived allyl systems to be less general in this process.
37. 4), concentrated, and then purified by flash chromatography.