Efficient Synthesis of Substituted Vinyl Ethers Using the Julia Olefination

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4851-4854

  Surprenant, Simon ^a   Chan, Wing Yan ^a   Berthelette, Carl ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BASE; ETHER DERIVATIVE; KETONE DERIVATIVE; REAGENT; SOLVENT; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; METHODOLOGY; OLEFINATION; PROCESS OPTIMIZATION; SYNTHESIS; TEMPERATURE;

EID: 0347683359     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035918k     Document Type: Article

References (34)

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12. For Wittig olefination see: (a) Wittig, G.; Schollkopf, U. Chem. Ber. 1954, 87, 1318. (b) Wittig, G.; Böll, W.; Krück, K.-H. Chem. Ber. 1962, 95, 2514. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. (e) Kelly, S. E. In Comprehensive Organic Synthesis; Trost B. M.; Fleming I., Eds; Pergamon: Oxford, 1991; Vol. 1, Part 3.1, pp 729.
13. For Wittig olefination see: (a) Wittig, G.; Schollkopf, U. Chem. Ber. 1954, 87, 1318. (b) Wittig, G.; Böll, W.; Krück, K.-H. Chem. Ber. 1962, 95, 2514. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. (e) Kelly, S. E. In Comprehensive Organic Synthesis; Trost B. M.; Fleming I., Eds; Pergamon: Oxford, 1991; Vol. 1, Part 3.1, pp 729.
14. For Wittig olefination see: (a) Wittig, G.; Schollkopf, U. Chem. Ber. 1954, 87, 1318. (b) Wittig, G.; Böll, W.; Krück, K.-H. Chem. Ber. 1962, 95, 2514. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. (e) Kelly, S. E. In Comprehensive Organic Synthesis; Trost B. M.; Fleming I., Eds; Pergamon: Oxford, 1991; Vol. 1, Part 3.1, pp 729.
15. For Wittig olefination see: (a) Wittig, G.; Schollkopf, U. Chem. Ber. 1954, 87, 1318. (b) Wittig, G.; Böll, W.; Krück, K.-H. Chem. Ber. 1962, 95, 2514. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. (e) Kelly, S. E. In Comprehensive Organic Synthesis; Trost B. M.; Fleming I., Eds; Pergamon: Oxford, 1991; Vol. 1, Part 3.1, pp 729.
16. For Wittig olefination see: (a) Wittig, G.; Schollkopf, U. Chem. Ber. 1954, 87, 1318. (b) Wittig, G.; Böll, W.; Krück, K.-H. Chem. Ber. 1962, 95, 2514. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. (e) Kelly, S. E. In Comprehensive Organic Synthesis; Trost B. M.; Fleming I., Eds; Pergamon: Oxford, 1991; Vol. 1, Part 3.1, pp 729.
17. For Horner-Emmons-Wadsworth olefination, see: (a) Kluge, A. F. Tetrahedron Lett. 1978, 19, 3629. (b) Kluge, A. F.; Cloudsdale, I. S. J. Org. Chem. 1979, 44, 4847.
18. For Horner-Emmons-Wadsworth olefination, see: (a) Kluge, A. F. Tetrahedron Lett. 1978, 19, 3629. (b) Kluge, A. F.; Cloudsdale, I. S. J. Org. Chem. 1979, 44, 4847.
19. See ref 4 and: Ferwanah, A.; Pressler, W.; Reichardt, C. Tetrahedron Lett. 1973, 3979.
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22. (c) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Bull. Soc. Chim. Fr. 1993, 130, 336.
23. For an excellent review on the modified Julia olefination, see: Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 23, 2563.
24. Other heterocycles have been used. For PT, see: (a) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26. (b) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285. For PYR, see: Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 5149 and 6619. For TBT, see: Kocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365.
25. Other heterocycles have been used. For PT, see: (a) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26. (b) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285. For PYR, see: Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 5149 and 6619. For TBT, see: Kocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365.
26. Other heterocycles have been used. For PT, see: (a) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26. (b) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285. For PYR, see: Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 5149 and 6619. For TBT, see: Kocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365.
27. Other heterocycles have been used. For PT, see: (a) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26. (b) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285. For PYR, see: Charette, A. B.; Berthelette, C.; St-Martin, D. Tetrahedron Lett. 2001, 42, 5149 and 6619. For TBT, see: Kocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365.
28. (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140.
29. (b) Blacklock, T. J.; Sohar, P.; Butcher, J. W.; Lamanec, T.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 1672.
30. Progress of the reaction was followed using a React-IR instrument, and all the reactions were completed between 15 and 90 min.
31. Addition of 12-C-4, TMEDA, and DMPU failed to improve the yields and the E:Z selectivity.
32. Barbier = base added to a mixture of sulfone and carbonyl; premetalate = base added to sulfone and then carbonyl added. Addition of base using a syringe pump over 30 min did not increase the yield or the E:Z ratio of vinyl ether 3.
33. 2 255.1385, found 255.1385.
34. 3N-treated silica gel to avoid decomposition to the homologated aldehydes.