Regio- and enantiospecific rhodium-catalyzed allylic substitution with an acyl anion equivalent

Organic Letters

Volumn 15, Issue 22, 2013, Pages 5626-5629

  Evans, P Andrew ^a   Oliver, Samuel ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ANION; KETONE; NAPHTHALENE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; ANIONS; CATALYSIS; KETONES; MOLECULAR STRUCTURE; NAPHTHALENES; RHODIUM; STEREOISOMERISM;

EID: 84887916896     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402336u     Document Type: Article

References (30)

1. Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591
2. Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105
3. Trost, B. M.; Jiang, C. Synthesis 2006, 369
4. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
5. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
6. Hong, A. Y.; Stoltz, B. M. Eur. J. Org. Chem. 2013, 2745
7. Stoltz, B. M.; Mohr, J. T. In Science of Synthesis; De Vries, J. G.; Molander, G. A.; Evans, P. A., Eds.; Thieme: Stuttgart, 2010; Vol. 3, p 567.
8. Oliver, S.; Evans, P. A. Synthesis 2013, 45, doi: 10.1055/s-0033-1338538.
9. Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918
10. Chen, G.; Kwong, F. Y.; Chan, H. O.; Yu, W.-Y.; Chan, A. S. C. Chem. Commun. 2006, 1413
11. García-Fortanet, J.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 8108
12. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195
13. Ge, S.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 16330
14. Chieffi, A.; Kamikawa, K.; Åhman, J.; Fox, J. M.; Buchwald, S. L. Org. Lett. 2001, 3, 1897
15. Huang, J.; Bunel, E.; Faul, M. M. Org. Lett. 2007, 9, 4343
16. Taylor, A. M.; Altman, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 9900
17. Kummer, D. A.; Chain, W. J.; Morales, M. R.; Quiroga, O.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 13231
18. Doyle, A. G.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 3701
19. Evans, P. A.; Oliver, S.; Chae, J. J. Am. Chem. Soc. 2012, 134, 19314
20. Kurono, N.; Yamaguchi, M.; Suzuki, K.; Ohkuma, T. J. Org. Chem. 2005, 70, 6530
21. Evans, P. A.; Leahy, D. K. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 10, pp 191-214.
22. Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581
23. For an example of a stereospecific iron-catalyzed allylic substitution of a tertiary allylic carbonate, see: Jegelka, M.; Plietker, B. Org. Lett. 2009, 11, 3462
24. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778
25. Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142
26. For a related process involving allylic acetates, see: Serra-Muns, A.; Guérinot, A.; Reymond, S.; Cossy, J. Chem. Commun. 2010, 46, 4178
27. The term conservation of enantiomeric excess (cee) = (ee of product/ee of starting material) × 100. Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761
28. For a recent review, see: Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
29. For a recent example of asymmetric spirolactonization of 1-naphthols catalyzed by a spirobiindane-based chiral hypervalent iodine species, see: Dohi, T.; Takenaga, N.; Nakae, T.; Toyoda, Y.; Yamasaki, M.; Shiro, M.; Fujioka, H.; Maruyama, A.; Kita, Y. J. Am. Chem. Soc. 2013, 135, 4558
30. 2ICl, the efficiency of this reaction is poor; see: Ozanne-Beaudenon, A.; Quideau, S. Angew. Chem., Int. Ed. 2005, 44, 7065