Diastereodivergent de-epimerization in catalytic asymmetric allylic alkylation

Angewandte Chemie - International Edition

Volumn 51, Issue 29, 2012, Pages 7314-7317

  Audisio, Davide ^a   Luparia, Marco ^a   Oliveira, Maria Teresa ^a   Klütt, Dina ^a   Maulide, Nuno ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

De epimerization; Diastereodivergence; Enantioselectivity; Palladium; Reaction mechanisms

Indexed keywords

ASYMMETRIC ALLYLIC ALKYLATIONS; DE-EPIMERIZATION; DE-RACEMIZATION; DIASTEREODIVERGENCE; DIASTEREOMERS; EPIMERS; HIGH SELECTIVITY; RACEMIC MIXTURES; REACTION MECHANISM;

PALLADIUM; STEREOCHEMISTRY;

ENANTIOSELECTIVITY;

EID: 84863823491     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202853     Document Type: Article

References (28)

1. H. Stecher, K. Faber, Synthesis 1997, 1-16
2. K. Faber, Chem. Eur. J. 2001, 7, 5004-5010
3. F. F. Huerta, A. B. E. Minidis, J. E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321-331
4. J. Steinreiber, K. Faber, H. Griengl, Chem. Eur. J. 2008, 14, 8060-8072
5. H. Pellissier, Tetrahedron 2011, 67, 3769-3802.
6. For examples of DYKAT type III, see
7. M. Edin, J. Steinreiber, J. E. Bäckvall, Proc. Natl. Acad. Sci. USA 2004, 101, 5761-5766
8. A. B. L. Fransson, Y. M. Xu, K. Leijondahl, J. E. Bäckvall, J. Org. Chem. 2006, 71, 6309-6316
9. B. Martín-Matute, J. E. Bäckvall, J. Org. Chem. 2004, 69, 9191-9195. See also page S58 of the Supporting Information.
10. E. J. Corey, J. Streith, J. Am. Chem. Soc. 1964, 86, 950-951.
11. M. Luparia, M. T. Oliveira, D. Audisio, F. Frébault, R. Goddard, N. Maulide, Angew. Chem. 2011, 123, 12840-12844
12. Angew. Chem. Int. Ed. 2011, 50, 12631-12635. For our previous work on Pd-mediated cyclobutene synthesis see
13. F. Frébault, M. Luparia, M. T. Oliveira, R. Goddard, N. Maulide, Angew. Chem. 2010, 122, 5807-5811
14. Angew. Chem. Int. Ed. 2010, 49, 5672-5676
15. M. Luparia, D. Audisio, N. Maulide, Synlett 2011, 735-740.
16. W. H. Pirkle, L. H. Mckendry, J. Am. Chem. Soc. 1969, 91, 1179-1186.
17. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353
18. J. F. Teichert, B. L. Feringa, Angew. Chem. 2010, 122, 2538-2582
19. Angew. Chem. Int. Ed. 2010, 49, 2486-2528.
20. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345.
21. B. M. Trost, D. L. VanVranken, Chem. Rev. 1996, 96, 395-422
22. Z. Lu, S. M. Ma, Angew. Chem. 2008, 120, 264-303
23. Angew. Chem. Int. Ed. 2008, 47, 258-297
24. B. M. Trost, T. Zhang, J. D. Sieber, Chem. Sci. 2010, 1, 427-440
25. G. Helmchen, U. Kazmaier, S. Förster, in Catalytic Asymmetric Synthesis (Ed.:, I. Ojima,), 3 rd ed., Wiley, Hoboken, 2010, pp. 497-641
26. J. C. Fiaud, J. Y. Legros, J. Org. Chem. 1987, 52, 1907-1911.
27. A. Pfaltz, W. Drury, Proc. Natl. Acad. Sci. USA 2004, 101, 5723-5726.
28. L. A. Evans, N. Fey, J. N. Harvey, D. Hose, G. C. Lloyd-Jones, P. Murray, A. G. Orpen, R. Osborne, G. J. J. Owen-Smith, M. Purdie, J. Am. Chem. Soc. 2008, 130, 14471-14473. When conditions for attenuation of ion-pair return were employed, only low yield and selectivity were observed for the product (see the Supporting Information for details).