The asymmetric ester enolate Claisen rearrangement as a suitable method for the synthesis of sterically highly demanding amino acids

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7945-7946

  Krebs, Achim ^a   Kazmaier, Uli ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030605051     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01764-9     Document Type: Article

References (19)

1. 1. Kazmaier, U. Angew. Chem. 1994, 106, 1096; Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
2. 1. Kazmaier, U. Angew. Chem. 1994, 106, 1096; Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
3. 2. (a) Kübel, B.; Höfle, G.; Steglich, W. Angew. Chem. 1975, 87, 64; Angew. Chem. Int. Ed. Engl.. 1975, 14, 58.
4. 2. (a) Kübel, B.; Höfle, G.; Steglich, W. Angew. Chem. 1975, 87, 64; Angew. Chem. Int. Ed. Engl.. 1975, 14, 58.
5. (b) Engel, N.; Kübel, B.; Stegtich, W. Angew. Chem. 1977, 89, 408; Angew. Chem. Int. Ed. Engl. 1977, 16, 394.
6. (b) Engel, N.; Kübel, B.; Stegtich, W. Angew. Chem. 1977, 89, 408; Angew. Chem. Int. Ed. Engl. 1977, 16, 394.
7. 3. (a) Bartlett, P, A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 619.
8. (b) Bartlett, P. A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933.
9. 4. For a review see: Kazmaier, U. Amino Acids in press.
10. 5. Kazmaier, U. J. Org. Chem. 1994, 59, 6667.
11. 6. Kazmaier, U., Krebs, A. Angew. Chem. 1995, 107, 2213. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012.
12. 6. Kazmaier, U., Krebs, A. Angew. Chem. 1995, 107, 2213. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012.
13. 7. Further examples of comparable asymmetric Claisen rearrangements: (a) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791.
14. (b) Corey, E. J.; Lee, D.; J. Am. Chem. Soc. 1991, 113, 4026.
15. (c) Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193.
16. (d) Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
17. 8. Kazmaier, U. Synlett 1995, 1138.
18. 9. (a) Kazmaier, U. J. Org. Chem. 1996, 61, 3694.
19. (b) Wipf, P. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds., Pergamon Press, Oxford, 1991, Vol.5, p 827 and literature cited herein.