Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4442-4448

  Metz, Peter ^a   Hungerhoff, Benno ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000853419     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970123a     Document Type: Article

References (23)

1. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
2. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
3. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
4. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
5. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
6. For recent reviews on the aliphatic Claisen rearrangement, see: (a) Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymm. 1996, 7, 1847-1882. (b) Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 827-873. (e) Blechert, S. Synthesis 1989, 71-82. (f) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
7. (a) For a preliminary report on this work, see: Metz, P.; Hungerhoff, B. GIT Fachz. Lab, 1996, 40, 690-691. (b) Metz, P.; Linz, C. Tetrahedron 1994, 50, 3951-3966. (c) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. (d) Metz, P.; Mues, C. Synlett 1990, 97-98. (e) Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
8. (a) For a preliminary report on this work, see: Metz, P.; Hungerhoff, B. GIT Fachz. Lab, 1996, 40, 690-691. (b) Metz, P.; Linz, C. Tetrahedron 1994, 50, 3951-3966. (c) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. (d) Metz, P.; Mues, C. Synlett 1990, 97-98. (e) Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
9. (a) For a preliminary report on this work, see: Metz, P.; Hungerhoff, B. GIT Fachz. Lab, 1996, 40, 690-691. (b) Metz, P.; Linz, C. Tetrahedron 1994, 50, 3951-3966. (c) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. (d) Metz, P.; Mues, C. Synlett 1990, 97-98. (e) Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
10. (a) For a preliminary report on this work, see: Metz, P.; Hungerhoff, B. GIT Fachz. Lab, 1996, 40, 690-691. (b) Metz, P.; Linz, C. Tetrahedron 1994, 50, 3951-3966. (c) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. (d) Metz, P.; Mues, C. Synlett 1990, 97-98. (e) Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
11. (a) For a preliminary report on this work, see: Metz, P.; Hungerhoff, B. GIT Fachz. Lab, 1996, 40, 690-691. (b) Metz, P.; Linz, C. Tetrahedron 1994, 50, 3951-3966. (c) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071-1080. (d) Metz, P.; Mues, C. Synlett 1990, 97-98. (e) Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
12. (a) Hattori, T.; Shijo, M.; Kumagai, S.; Miyano, S. Chem. Express 1991, 6, 335-338.
13. (b) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613-622.
14. For a review on auxiliary induced enantioseleetive Claisen rearrangements, see ref 1 a. See also: (a) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229-1230. (b) Wilken, J.; Wallbaum, S.; Saak, W.; Haase, D.; Pohl, S.; Patkar, L. N.; Dixit, A. N.; Chittari, P.; Rajappa, S.; Martens, J. Liebigs Ann. 1996, 927-934.
15. For a review on auxiliary induced enantioseleetive Claisen rearrangements, see ref 1 a. See also: (a) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229-1230. (b) Wilken, J.; Wallbaum, S.; Saak, W.; Haase, D.; Pohl, S.; Patkar, L. N.; Dixit, A. N.; Chittari, P.; Rajappa, S.; Martens, J. Liebigs Ann. 1996, 927-934.
16. For enantioseleetive Claisen rearrangements promoted by chiral Lewis acids, see: Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165-1166.
17. Newcomb, M.; Esker, J. L. Tetrahedron. Lett. 1991, 32, 1035-1038.
18. Gluchowski, C.; Tiner-Harding, T.; Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. J. Org. Chem. 1984, 49, 2650-2652.
19. In order to rapidly prepare all four diastereomeric Claisen rearrangement products for analytical reasons, we also subjected imidates 3 to a thermal isomerization (see ref 2e) in refluxing decalin. As anticipated, these reactions proceeded cleanly and syn selectively but without significant auxiliary induction.
20. Metz, P. Tetrahedron 1993, 49, 6367-6374.
21. Oppolzer, W.; Kingma, A. J.; Poli, G. Tetrahedron 1989, 45, 479-488.
22. Corey, E. J.; Lee, D.-H. J. Am. Chem. Soc. 1991, 113, 4026-4028 and Supporting Information.
23. As reference substances, racemic acids 10 prepared by Ireland-Claisen rearrangement were used, see: Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.