Asymmetric Sulfur Ylide Mediated Aziridination: Application in the Synthesis of the Side Chain of Taxol

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3987-3990

  Aggarwal, Varinder K ^a   Vasse, Jean Luc ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; AZIRIDINE DERIVATIVE; BENZOYLAZIRIDINE; OXAZOLIDINONE DERIVATIVE; PACLITAXEL; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; AZIRIDINATION; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOSPECIFICITY;

AZIRIDINES; MODELS, CHEMICAL; PACLITAXEL; SULFUR COMPOUNDS;

EID: 0242628373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035554w     Document Type: Article

References (36)

1. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
2. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
3. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
4. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
5. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
6. Reviews on applications and synthesis: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 607. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
7. Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
8. (a) Olofsson, B.; Somfai, P. J. Org. Chem. 2002, 67, 8574 (and references therein).
9. (b) Olofsson, B.; Khamrai, U.; Somfai, P. Org. Lett. 2000, 2, 4087.
10. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433.
11. Aggarwal, V. K. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 679.
12. For recent references on the sulfur ylide route to aziridines, see: (a) Saito, T.; Akiba, D.; Sakairi, M. Tetrahedron Lett. 2001, 42, 5451. (b) Aggarwal, V. K.; Ferrara, M.; O'Brien, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 1635. (c) Yang, X.-F.; Zhang, M.-J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2002, 67, 8097.
13. For recent references on the sulfur ylide route to aziridines, see: (a) Saito, T.; Akiba, D.; Sakairi, M. Tetrahedron Lett. 2001, 42, 5451. (b) Aggarwal, V. K.; Ferrara, M.; O'Brien, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 1635. (c) Yang, X.-F.; Zhang, M.-J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2002, 67, 8097.
14. For recent references on the sulfur ylide route to aziridines, see: (a) Saito, T.; Akiba, D.; Sakairi, M. Tetrahedron Lett. 2001, 42, 5451. (b) Aggarwal, V. K.; Ferrara, M.; O'Brien, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 1635. (c) Yang, X.-F.; Zhang, M.-J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2002, 67, 8097.
15. Application of the asymmetric epoxidation process in the synthesis of CDP 840 was recently described: Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem., Int. Ed. 2003, 42, 3274.
16. For reviews, see: (a) Kingston, D. G. I. Chem. Commun. 2001, 867. (b) Kingston, D. G. I. J. Nat. Prod. 2000, 63, 726. (c) Nicolaou, K. C.; Dai, W.-M. ; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
17. For reviews, see: (a) Kingston, D. G. I. Chem. Commun. 2001, 867. (b) Kingston, D. G. I. J. Nat. Prod. 2000, 63, 726. (c) Nicolaou, K. C.; Dai, W.-M. ; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
18. For reviews, see: (a) Kingston, D. G. I. Chem. Commun. 2001, 867. (b) Kingston, D. G. I. J. Nat. Prod. 2000, 63, 726. (c) Nicolaou, K. C.; Dai, W.-M. ; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
19. The most direct route is attributed to Sharpless: Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
20. (a) Jacobsen, E. N. Deng, L.; Furukawa, Y.; Martinez, L. E. Tetrahedron Lett. 1994, 50, 4323.
21. (b) Denis, J.-N.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46.
22. Aggarwal, V. K.; Alonso, E. Unpublished results.
23. Katritzky, A. R.; Fan, W.-Q.; Black, M.; Pernak, J. J. Org. Chem. 1992, 57, 547.
24. Kupfer, R.; Meier, S.; Würthwein, E.-U. Synthesis 1984, 688.
25. Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Richardson, J.; Stenson, R. A.; Studley, J.; Vasse, J.-L.; Winn, C. J. Am. Chem. Soc. 2003, 125, 10926.
26. 4 (see ref 6).
27. Silica gel has been reported to effect rearrangement of unsaturated acyl aziridines into oxazolines: Lindström, U. M.; Somfai, P. J. Am. Chem. Soc. 1997, 119, 8385.
28. Treatment of the pure cis-aziridine with acetic acid resulted in a 3/1 mixture of trans/cis oxazoline, whereas pure trans-aziridine gave transoxazoline only. This showed that rearrangement of the cis-aziridine is not stereospecific.
29. Cabri, W.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 1996, 37, 4785-4786.
30. (a) Carlsen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
31. (b) Boger, D. L.; Lee, R. J.; Bournaud, P.-Y.; Meier, P. J. Org. Chem. 2000, 65, 6770-6772.
32. Murakami, N.; Tamura, S.; Wang, W.; Takagi, T.; Kobayashi, M. Tetrahedron 2001, 57, 4323-4336.
33. Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497.
34. The use of CsF or TBAT on their own were much less effective than the combination.
35. Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569.
36. Aggarwal, V. K.; Charmant, J. P. H.; Ciampi, C.; Hornby, J. M.; O'Brien, C. J.; Hynd, G.; Parsons, R. J. Chem. Soc., Perkin Trans, 1 2001, 3159.