Enantioselective Suzuki reactions: Catalytic asymmetric synthesis of compounds containing quaternary carbon centers

Angewandte Chemie - International Edition

Volumn 43, Issue 10, 2004, Pages 1249-1251

  Willis, Michael C ^a   Powell, Luke H W ^a   Claverie, Christelle K ^a   Watson, Simon J ^b  

^a University of Bath   (United Kingdom)

^b NOVARTIS HORSHAM RESEARCH CENTRE   (United Kingdom)

Author keywords

Asymmetric catalysis; Cross coupling; Enantioselectivity; Palladium

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; SUBSTRATES;

ENANTIOSELECTIVE DESYMMETRIZATION; PROCHIRAL DITRIFLATES; QUATERNERY CARBON CENTER;

REACTION KINETICS;

BORONIC ACID DERIVATIVE; CARBON; PALLADIUM COMPLEX; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 4544335033     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352648     Document Type: Article

References (31)

1. For reviews of enantioselective palladium-catalyzed coupling reactions, see: a) T. Hayashi in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 887-907;
2. b) M. Ogasawara, T. Hayashi in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000, pp. 651-674;
3. c) C. G. Frost in Rodd's Chemistry of Carbon Compounds, Vol. 5, 2nd ed. (Ed.: M. Sainsbury), Elsevier, Amsterdam, 2001, pp. 315-350.
4. For recent reviews of enantioselective Heck reactions, see: a) M. Shibasaki, E. M. Vogl in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 457-487
5. b) M. Shibasaki, E. M. Vogl, J. Organomet. Chem. 1999, 576, 1-15;
6. c) O. Loiseleur, M. Hayashi, M. Keenan, N. Schmees, A. Pfaltz, J. Organomet. Chem. 1999, 576, 16-22;
7. d) Y. Donde, L. E. Overman in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000, pp. 675-697.
8. J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051-12052.
9. A. N. Cammidge, K. V. L. Crépy, Chem. Commun. 2000, 1723-1724.
10. For the application of an antropo-enantioselective Suzuki reaction to the synthesis of the analogues of rhazinilam, see: A. Herrbach, A. Marinetti, O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2003, 68, 4897-4905.
11. a) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8156;
12. b) T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101-9102;
13. c) T. Kamikawa, T. Hayashi, Tetrahedron 1999, 55, 3455-3466.
14. a) M. Uemura, H. Nishimura, T. Hayashi, J. Organomet. Chem. 1994, 473, 129-137.
15. For a palladium-catalyzed carbonylation route to planar chiral systems, see: b) B. Gotov, H.-G. Schmalz, Org. Lett. 2001, 3, 1753-1756.
16. For a desymmetrization-based enantioselective intramolecular Suzuki coupling that delivers products with selectivities up to 31% ee, see: S. Y. Cho, M. Shibasaki, Tetrahedron: Asymmetry 1998, 9, 3751-3754.
17. For a review of enantioselective desymmetrization, see: M. C. Willis, J. Chem. Soc. Perkin Trans. 1 1999, 1765-1784.
18. For reviews of Suzuki reactions, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
19. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
20. For the synthesis of 1a and its use in achiral Suzuki couplings, see: M. C. Willis, C. K. Claverie, Tetrahedron Lett. 2001, 42, 5105-5107.
21. For the use of substrates related to 1a in enantioselective intramolecular Heck reactions, see: S. Bräse, Synlett 1999, 1654-1656.
22. 3]/MeO-MOP (dba = trans,trans-dibenzylideneacetone) and CsF, dioxane conditions resulted in 30% yield and 51% ee.
23. S. Breeden, D. J. Cole-Hamilton, D. F. Foster, G. J. Schwarz, M. Wills, Angew. Chem. 2000, 112, 4272-4274; Angew. Chem. Int. Ed. 2000, 39, 4106-4108.
24. S. Breeden, D. J. Cole-Hamilton, D. F. Foster, G. J. Schwarz, M. Wills, Angew. Chem. 2000, 112, 4272-4274; Angew. Chem. Int. Ed. 2000, 39, 4106-4108.
25. The absolute configuration of compound 5 was established by X-ray diffraction analysis of the recrystallized material (97% ee). The absolute configurations of the remaining adducts are assigned by analogy.
26. For reviews detailing the enantioselective construction of quaternary centers, see: a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4587-4591;
27. For reviews detailing the enantioselective construction of quaternary centers, see: a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4587-4591;
28. b) E.J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
29. b) E.J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
30. c) K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
31. M. C. Willis, C. K. Claverie, M. F. Mahon, Chem. Commun. 2002, 832-833.