Simple preparation of trans-epoxides via ylide intermediates

Synthesis

Volumn , Issue 8, 2005, Pages 1378-1382

  Aggarwal, Varinder K ^a   Aragoncillo, Cristina ^a   Winn, Caroline L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Asymmetric catalysis; Diazo compounds; Epoxidations; Epoxides; Sulfur ylides

Indexed keywords

ALDEHYDES; BENZENE; SALTS; SODIUM COMPOUNDS; STEREOCHEMISTRY;

BENZALDEHYDE TOSYLHYDRAZONE SODIUM SALTS; ENANTIOMERS; EPOXIDES; REACTIVE INTERMEDIATES;

OXIDES;

AZO COMPOUND; BENZALDEHYDE; BICYCLO COMPOUND; CAMPHOR DERIVATIVE; EPOXIDE; HYDRAZONE DERIVATIVE; SULFIDE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 20344389503     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834885     Document Type: Article

References (24)

1. Rossiter, B. E. Asymmetric Synthesis, Vol. 5; Morrison, J. D., Ed.; Academic Press: New York, 1985, 193-246.
2. Smith, J. G. Synthesis 1984, 629.
3. (a) Katsuki, T. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 621-648.
4. (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 649-677.
5. (c) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
6. (a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
7. (b) Aggarwal, V. K. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 679-693.
8. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
9. (a) Aggarwal, V. K.; Ford, J. G.; Fonquerna, S.; Adams, H.; Jones, R. V. H.; Fieldhouse, R. J. Am. Chem. Soc. 1998, 120, 8328.
10. (b) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004.
11. (c) Aggarwal, V. K. Synlett 1998, 329.
12. (d) Studley, J. R.; Aggarwal, V. K. (Astra Zeneca) WO98/516666, 1998.
13. Aggarwal, V. K.; Abdel-Rahman, H.; Fan, L.; Jones, R. V. H.; Standen, M. C. H. Chem.-Eur. J. 1996, 2, 1024.
14. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: London, 1986.
15. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem. Int. Ed. 2001, 40, 1430.
16. 9
17. Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, I25, 10926.
18. For a review on sulfur ylide rearrangements, see: Marko, I. E. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergammon: Oxford, 1979, 913-974.
19. Aggarwal, V. K.; Patel, M.; Studley, J. Chem. Commun. 2002, 1514.
20. Rhodium (II) acetate was prepared from rhodium trichloride trihydrate and anhyd NaOAc in glacial HOAc and EtOH: Rempel, G. A.; Legzdins, P.; Smith, H.; Wilkinson, G. Inorg. Synth. 1971, 13, 90.
21. The structure of 6 was confirmed by preparation of a reference sample using the tosylhydrazone salt 8 and benzyl bromide in DMF: Nozaki, H.; Noyori, R.; Sisido, K. Tetrahedron 1964, 20, 1125.
22. For a full discussion of the factors controlling enantio- and diastereoselectivity, see: Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003, 2644.
23. McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W.; Kreil, C. L.; LeRoux, J. P.; Mooring, A. M.; West, P. R. J. Am. Chem. Soc. 1987, 109, 2456.
24. Imuta, M.; Ziffer, H. J. Org. Chem. 1979, 44, 2505.