A Mild Protocol for Allylation and Highly Diastereoselective Syn or Anti Crotylation of Aldehydes in Biphasic and Aqueous Media Utilizing Potassium Allyl- and Crotyltrifluoroborates

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3827-3830

  Thadani, Avinash N ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0037594874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026619i     Document Type: Article

References (43)

1. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
2. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1-53 and references therein.
3. (a) Curran, D. P.; Luo, Z. Y.; Degenkolb, P. Biorg. Med. Chem. Lett. 1998, 8, 2403-2408.
4. (b) Curran, D. P.; Hadida, S.; Mu, H. J. Org. Chem. 1997, 62, 6714-6715.
5. (c) For a review on solution-phase combinatorial chemistry, see: An, H. Y.; Cook, P. D. Chem. Rev. 2000, 100, 3311-3340.
6. (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772.
7. (b) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media: Wiley & Sons: New York, 1997.
8. For recent reviews, see: (a) Li, C. J. Tetrahedron 1996, 52, 5643-5668. (b) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741-760.
9. For recent reviews, see: (a) Li, C. J. Tetrahedron 1996, 52, 5643-5668. (b) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741-760.
10. For recent examples, see: (a) Lu, W.; Chan, T. K. J. Org. Chem. 2001, 66, 3467-3473. (b) Loh, T.-P.; Zhou, J. R.; Yin, Z. Org Lett. 1999, 1, 1855-1857. (c) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217-224. Raquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804. (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
11. For recent examples, see: (a) Lu, W.; Chan, T. K. J. Org. Chem. 2001, 66, 3467-3473. (b) Loh, T.-P.; Zhou, J. R.; Yin, Z. Org Lett. 1999, 1, 1855-1857. (c) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217-224. Raquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804. (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
12. For recent examples, see: (a) Lu, W.; Chan, T. K. J. Org. Chem. 2001, 66, 3467-3473. (b) Loh, T.-P.; Zhou, J. R.; Yin, Z. Org Lett. 1999, 1, 1855-1857. (c) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217-224. Raquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804. (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
13. For recent examples, see: (a) Lu, W.; Chan, T. K. J. Org. Chem. 2001, 66, 3467-3473. (b) Loh, T.-P.; Zhou, J. R.; Yin, Z. Org Lett. 1999, 1, 1855-1857. (c) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217-224. (d) Raquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804. (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
14. For recent examples, see: (a) Lu, W.; Chan, T. K. J. Org. Chem. 2001, 66, 3467-3473. (b) Loh, T.-P.; Zhou, J. R.; Yin, Z. Org Lett. 1999, 1, 1855-1857. (c) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217-224. Raquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804. (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228-3229.
15. For recent examples, see: (a) Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (b) Loh, T.-P.; Xu, J.; Hu, Q.-Y.; Vittal, J. J. Tetrahedron: Asymmetry 2000, 11, 1565-1569. Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452-4455. (d) Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y. J. Org. Chem. 2000, 65, 494-498.
16. For recent examples, see: (a) Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (b) Loh, T.-P.; Xu, J.; Hu, Q.-Y.; Vittal, J. J. Tetrahedron: Asymmetry 2000, 11, 1565-1569. Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452-4455. (d) Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y. J. Org. Chem. 2000, 65, 494-498.
17. For recent examples, see: (a) Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (b) Loh, T.-P.; Xu, J.; Hu, Q.-Y.; Vittal, J. J. Tetrahedron: Asymmetry 2000, 11, 1565-1569. (c) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452-4455. (d) Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y. J. Org. Chem. 2000, 65, 494-498.
18. For recent examples, see: (a) Loh, T.-P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (b) Loh, T.-P.; Xu, J.; Hu, Q.-Y.; Vittal, J. J. Tetrahedron: Asymmetry 2000, 11, 1565-1569. Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452-4455. (d) Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y. J. Org. Chem. 2000, 65, 494-498.
19. For recent examples, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208-5216. (b) Márquez, F.; Llebaria, A.; Delgado, A. Org. Lett. 2000, 2, 547-549. (c) Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737.
20. For recent examples, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208-5216. (b) Márquez, F.; Llebaria, A.; Delgado, A. Org. Lett. 2000, 2, 547-549. (c) Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737.
21. For recent examples, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208-5216. (b) Márquez, F.; Llebaria, A.; Delgado, A. Org. Lett. 2000, 2, 547-549. (c) Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737.
22. Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230-3236.
23. Roush, W. R. In Houben-Weyl, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart Germany, 1995; Vol. E21b, pp 1410-1486 and references therein.
24. (b) Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, 1995.
25. (a) Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990-998.
26. (b) Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289-4292.
27. (c) Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099-9103.
28. (d) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683-1686.
29. 2), removal of the solvent, and passage of the resulting crude reaction mixture through a short plug of silica gel (EtOAc as the eluent) in order to remove the PTC.
30. For a recent monograph on phase transfer catalysis, see: Handbook of Phase Transfer Catalysis; Sasson, Y., Neumann, R. Eds.; Blackie Academic & Professional: London, 1997.
31. Reaction of specific indium reagents derived from functionalized allyl bromides with aldehydes proceeds in some cases with high diastereoselectivity, see: (a) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538. (b) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333-5338. (c) Loh, T.-P.; Li, X.-R. Eur. J. Org. Chem. 1999, 1893-1899. (d) Canac, Y.; Levoirier, E.; Lubineau, A. J. Org. Chem. 2001, 66, 3206-3210.
32. Reaction of specific indium reagents derived from functionalized allyl bromides with aldehydes proceeds in some cases with high diastereoselectivity, see: (a) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538. (b) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333-5338. (c) Loh, T.-P.; Li, X.-R. Eur. J. Org. Chem. 1999, 1893-1899. (d) Canac, Y.; Levoirier, E.; Lubineau, A. J. Org. Chem. 2001, 66, 3206-3210.
33. Reaction of specific indium reagents derived from functionalized allyl bromides with aldehydes proceeds in some cases with high diastereoselectivity, see: (a) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538. (b) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333-5338. (c) Loh, T.-P.; Li, X.-R. Eur. J. Org. Chem. 1999, 1893-1899. (d) Canac, Y.; Levoirier, E.; Lubineau, A. J. Org. Chem. 2001, 66, 3206-3210.
34. Reaction of specific indium reagents derived from functionalized allyl bromides with aldehydes proceeds in some cases with high diastereoselectivity, see: (a) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538. (b) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333-5338. (c) Loh, T.-P.; Li, X.-R. Eur. J. Org. Chem. 1999, 1893-1899. (d) Canac, Y.; Levoirier, E.; Lubineau, A. J. Org. Chem. 2001, 66, 3206-3210.
35. Not surprisingly, the use of chiral PTCs did not result in enantioselective addition. For leading references on chiral PTCs, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
36. Compound 6 was isolated as a clear, colorless solid contaminated with approximately 1% of tetra n-butylammonium tetrafluoroborate.
37. Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 103, 1969-1975 and references therein.
38. Le Serre, S.; Guillemin, J. C. Organometallics 1997, 16, 5844-5848.
39. For examples of the common ion effect, see: (a) Bolton, J. L.; McClelland, R. A. Can. J. Chem. 1989, 67, 1139-1143. (b) Gun'kin, I. F.; Butin, K. P.; Beletskaya, I. P.; Reutov, O. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1978, 1297-1300. (c) Hughes, E. D.; Ingold, C. K.; Mok, S. F.; Pocker, Y. J. Chem. Soc. 1957, 1238-1255.
40. For examples of the common ion effect, see: (a) Bolton, J. L.; McClelland, R. A. Can. J. Chem. 1989, 67, 1139-1143. (b) Gun'kin, I. F.; Butin, K. P.; Beletskaya, I. P.; Reutov, O. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1978, 1297-1300. (c) Hughes, E. D.; Ingold, C. K.; Mok, S. F.; Pocker, Y. J. Chem. Soc. 1957, 1238-1255.
41. For examples of the common ion effect, see: (a) Bolton, J. L.; McClelland, R. A. Can. J. Chem. 1989, 67, 1139-1143. (b) Gun'kin, I. F.; Butin, K. P.; Beletskaya, I. P.; Reutov, O. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1978, 1297-1300. (c) Hughes, E. D.; Ingold, C. K.; Mok, S. F.; Pocker, Y. J. Chem. Soc. 1957, 1238-1255.
42. Omoto, K.; Fujimoto, H. J. Org. Chem. 1998, 63, 8331-8336.
43. Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868-1874.