A new highly asymmetric chelation-controlled heck arylation

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3430-3431

  Nilsson, Peter ^a   Larhed, Mats ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION COMPOUND; KETONE;

ARTICLE; ARYLATION; CHELATION; CHEMICAL BOND; DIASTEREOISOMER; HECK REACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037467473     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029646c     Document Type: Article

References (31)

1. (a) Hamada, T.; Buchwald, S. L. Org. Lett. 2002, 4, 999-1001.
2. (b) Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
3. (c) Fox, J. M.; Huang, X. H.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
4. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
5. (e) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
6. (a) Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268.
7. (b) A ̊hman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918-1919.
8. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217-8225.
9. (a) Heck, R. F. Org. React. 1982, 27, 345-363.
10. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
11. (c) Larhed, M.; Hallberg, A. In Handbook of Organo-Palladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1133-1178.
12. (d) Shibasaki, M.; Miyazaki, F. In Handbook of Organo-Palladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1283-1315.
13. For examples of related chelation-controlled Heck reactions, see: (a) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585. (b) Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603-3606. (c) Larhed, M.; Andersson, C. M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212-217. (d) Andersson, C. M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757-5761.
14. For examples of related chelation-controlled Heck reactions, see: (a) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585. (b) Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603-3606. (c) Larhed, M.; Andersson, C. M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212-217. (d) Andersson, C. M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757-5761.
15. For examples of related chelation-controlled Heck reactions, see: (a) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585. (b) Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603-3606. (c) Larhed, M.; Andersson, C. M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212-217. (d) Andersson, C. M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757-5761.
16. For examples of related chelation-controlled Heck reactions, see: (a) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585. (b) Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603-3606. (c) Larhed, M.; Andersson, C. M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212-217. (d) Andersson, C. M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757-5761.
17. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
18. For examples of metal chelating chiral auxiliary in non-Heck transformations, see: (a) Westwell, A. D.; Williams, J. M. J. Tetrahedron 1997, 53, 13063-13078. (b) Breit, B. Chem.-Eur. J. 2000, 6, 1519-1524.
19. For examples of metal chelating chiral auxiliary in non-Heck transformations, see: (a) Westwell, A. D.; Williams, J. M. J. Tetrahedron 1997, 53, 13063-13078. (b) Breit, B. Chem.-Eur. J. 2000, 6, 1519-1524.
20. 2O (0.2 mL) were mixed in 2 mL of DMF and heated at a given time and temperature (Table 1).
21. Reviews covering the creation of chiral quaternary centers: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
22. Reviews covering the creation of chiral quaternary centers: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
23. The proposed structure of the π-intermediate D was obtained by semimanual modeling, see Supporting Information.
24. (a) Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505-2079.
25. (b) McCrindle, R.; Ferguson, G.; Khan, M. A.; McAlees, A. J.; Ruhl, B. L. J. Chem. Soc., Dalton Trans. 1981, 986-991.
26. (c) Thorn, D. L.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079-2090.
27. For a discussion regarding the diastereoselectivity, see Supporting Information.
28. 17O NMR and conformation of cyclic vinyl ethers, see: (a) Taskinen, E.; Ora, M. Magn. Reson. Chem. 1995, 33, 239-243. (b) Taskinen, E.; Hellman, J. Magn. Reson. Chem. 1994, 32, 353-357.
29. 17O NMR and conformation of cyclic vinyl ethers, see: (a) Taskinen, E.; Ora, M. Magn. Reson. Chem. 1995, 33, 239-243. (b) Taskinen, E.; Hellman, J. Magn. Reson. Chem. 1994, 32, 353-357.
30. We have previously shown that chelating tertiary amine tethered vinyl ethers are more reactive than the noncoordinating alkyl counterparts in Heck arylations (see refs 3 and 5c,d).
31. Westwell, A. D.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1-2.