Construction of quaternary carbon centers by using substitution of γ,γ-disubstituted secondary allylic picolinates with alkylcopper reagents

Tetrahedron Letters

Volumn 54, Issue 35, 2013, Pages 4629-4632

  Feng, Chao ^a   Kaneko, Yuki ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkylcopper reagents; Allylic substitution; Chirality transfer; Quaternary carbon; Regioselectivity

Indexed keywords

ALKENE; ALKYL GROUP; BENZYL DERIVATIVE; BROMIDE; CARBON; COPPER BROMIDE; COPPER DERIVATIVE; MAGNESIUM BROMIDE; MAGNESIUM DERIVATIVE; MENDELEVIUM; PICOLINIC ACID; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ENANTIOMER; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 84880850491     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.046     Document Type: Article

References (33)

1. Selected reviews: J. Christoffers, and A. Mann Angew. Chem., Int. Ed. 40 2001 4591
2. J. Christoffers, and A. Baro Angew. Chem., Int. Ed. 42 2003 1688
3. A.H. Hoveyda, A.W. Hird, and M.A. Kacprzynski Chem. Commun. 2004 1779
4. B.M. Trost, and C. Jiang Synthesis 2006 369
5. S.R. Harutyunyan, T. den Hartog, K. Geurts, A.J. Minnaard, and B.L. Feringa Chem. Rev. 108 2008 2824
6. B. Breit, and Y. Schmidt Chem. Rev. 108 2008 2928
7. Z. Lu, and S. Ma Angew. Chem., Int. Ed. 47 2008 258
8. A. Alexakis, J.E. Bäckvall, N. Krause, O. Pàmies, and M. Diéguez Chem. Rev. 108 2008 2796
9. J.P. Das, J. Prakash, and I. Marek Chem. Commun. 2011 4593
10. J.D. Egbert, C.S.J. Cazin, and S.P. Nolan Catal. Sci. Technol. 3 2013 912
11. M. Shimizu Angew. Chem., Int. Ed. 50 2011 5998
12. A.Y. Hong, and B.M. Stoltz Eur. J. Org. Chem. 2013 2745
13. For example: B.M. Trost, and M.L. Crawley Chem. Rev. 103 2003 2921
14. D. Soorukram, and P. Knochel Org. Lett. 9 2007 1021
15. M. Arbour, S. Roy, C. Godbout, and C. Spino J. Org. Chem. 74 2009 3806
16. F. Gao, Y. Lee, K. Mandai, and A.H. Hoveyda Angew. Chem., Int. Ed. 49 2010 8370
17. R.P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H.K. Scott, and V.K. Aggarwal Angew. Chem., Int. Ed. 50 2011 3760
18. M.J. Schnermann, and L.E. Overman Angew. Chem., Int. Ed. 51 2012 9576
19. M.J. Schnermann, N.L. Untiedt, G. Jiménez-Osés, K.N. Houk, and L.E. Overman Angew. Chem., Int. Ed. 51 2012 9581
20. A. Lumbroso, M.L. Cooke, and B. Breit Angew. Chem., Int. Ed. 52 2013 1890
21. B. Breit, P. Demel, and C. Studte Angew. Chem., Int. Ed. 43 2004 3786
22. B. Breit, P. Demel, D. Grauer, and C. Studte Chem. Asian J. 1 2006 586
23. N. Harrington-Frost, H. Leuser, M.I. Calaza, F.F. Kneisel, and P. Knochel Org. Lett. 5 2003 2111
24. H. Leuser, S. Perrone, F. Liron, F.F. Kneisel, and P. Knochel Angew. Chem., Int. Ed. 44 2005 4627
25. S. Perrone, and P. Knochel Org. Lett. 9 2007 1041
26. C. Spino, and C. Beaulieu Angew. Chem., Int. Ed. 39 2000 1930
27. Y. Kiyotsuka, H.P. Acharya, Y. Katayama, T. Hyodo, and Y. Kobayashi Org. Lett. 10 2008 1719
28. Y. Kiyotsuka, and Y. Kobayashi Tetrahedron Lett. 49 2008 7256
29. Y. Kiyotsuka, Y. Katayama, H.P. Acharya, T. Hyodo, and Y. Kobayashi J. Org. Chem. 2009 1939 74
30. Y. Kaneko, Y. Kiyotsuka, H.P. Acharya, and Y. Kobayashi Chem. Commun. 2010 5482
31. F. Chao, and Y. Kobayashi J. Org. Chem. 78 2013 3755
32. H.O. House, W.L. Respess, and G.M. Whitesides J. Org. Chem. 31 1966 3128
33. N. Fujii, K. Nakai, H. Habashita, H. Yoshizawa, T. Ibuka, F. Garrido, A. Mann, Y. Chounan, and Y. Yamamoto Tetrahedron Lett. 34 1993 4227