Access to chiral α-bromo and α-H-substituted tertiary allylic alcohols via copper(i) catalyzed 1,2-addition of Grignard reagents to enones

Organic and Biomolecular Chemistry

Volumn 10, Issue 14, 2012, Pages 2878-2884

  Madduri, Ashoka V R ^a   Minnaard, Adriaan J ^a   Harutyunyan, Syuzanna R ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; ASYMMETRIC SYNTHESIS; DIHYDROFURANS; GRIGNARD REAGENT; NATURAL PRODUCTS; ORGANIC CHEMISTRY; ORGANOMETALLIC REAGENT; TERTIARY ALCOHOLS;

CATALYSIS; COPPER; KETONES; ORGANOMETALLICS;

STEREOCHEMISTRY;

ALKENE; ALLYL ALCOHOL; BROMINE DERIVATIVE; COPPER; KETONE; PROPANOL;

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

ALKENES; BROMINE COMPOUNDS; CATALYSIS; COPPER; KETONES; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM;

EID: 84864383693     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob25080b     Document Type: Article

References (50)

1. J. L. Stymiest V. Bagutski R. M. French V. K. Aggarwal Nature 2008 456 778
2. M. Shibasaki M. Kanai Chem. Rev. 2008 108 2853
3. Handbook of Homogeneous Hydrogenation, ed., J. G. de Vries, and, C. J. Elsevier, 2007, Wiley-VCH, Weinheim
4. B. M. Trost M. L. Crawley Chem. Rev. 2003 103 2921
5. M. Althaus A. Mahmood J. Ramón Suárez S. P. Thomas V. K. Aggarwal J. Am. Chem. Soc. 2010 132 4025
6. E. Skucas M.-Y. Ngai V. Komanduri M. J. Krische Acc. Chem. Res. 2007 40 1394
7. H. Jiang N. Holub K. A. Jorgensen Proc. Natl. Acad. Sci. U. S. A. 2010 107 20630
8. K. Kamata K. Yamaguchi N. Mizuno Chem.-Eur. J. 2004 10 4728
9. K. A. Jorgensen Chem. Rev. 1989 89 431
10. W. Adam T. Wirth Acc. Chem. Res. 1999 32 703
11. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Comprehensive Asymmetric Catalysis: Suppl. 2, Springer-Verlag, Berlin, 2004
12. P. J. Walsh and M. C. Kozlowski, Fundamentals of Asymmetric Catalysis, University Science Books, California, 2009
13. J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, California, 2010
14. R. Noyori M. Kitamura Angew. Chem., Int. Ed. Engl. 1991 30 49 69
15. P. J. Walsh Acc. Chem. Res. 2003 36 739
16. M. R. Luderer W. F. Bailey M. R. Luderer J. D. Fair R. J. Dancer M. B. Sommer Tetrahedron: Asymmetry 2009 20 981
17. L. Pu H.-B. Yu Chem. Rev. 2001 101 757
18. C. M. Binder B. Singaram Org. Prep. Proced. Int. 2011 43 139
19. M. Hatano K. Ishihara Synthesis 2008 11 1647
20. O. Riant J. Hannedouche Org. Biomol. Chem. 2007 5 873
21. P. I. Dosa G. Fu J. Am. Chem. Soc. 1998 120 445
22. D. J. Ramón M. Yus Tetrahedron Lett. 1998 39 1239
23. H. Li P. J. Walsh J. Am. Chem. Soc. 2004 126 6538
24. D. J. Ramón M. Yus Angew. Chem., Int. Ed. 2004 43 284
25. S.-J. Jeon H. Li C. García L. K. LaRochelle P. J. Walsh J. Org. Chem. 2005 70 448
26. E. F. DiMauro M. C. Kozlowski J. Am. Chem. Soc. 2002 124 2668
27. D. K. Friel M. L. Snapper A. H. Hoveyda J. Am. Chem. Soc. 2008 130 9942
28. M. Hatano T. Miyamoto K. Ishihara Org. Lett. 2007 9 4535
29. Y. Muramatsu and T. Harada, Angew. Chem., Int. Ed., 2008, 47, 1088
30. Y. Muramatsu S. Kanehira M. Tanigawa Y. Miyawaki T. Harada Bull. Chem. Soc. Jpn. 2010 83 19
31. A. Börner, in Trivalent Phosphorus Compounds in Asymmetric Catalysis: Synthesis and Applications, ed., W. Chen, and, H. U. Blaser, Wiley-VCH, 2008, p. 359
32. A. V. R. Madduri A. J. Minnaard S. R. Harutyunyan Chem. Commun. 2012 48 1478 10.1039/c1cc16725a
33. H. Gilman J. M. Straley Recl. Trav. Chim. Pays-Bas 1936 55 821
34. N. Krause, Modern Organocopper Chemistry, Wiley-VCH, Weinheim, 2002
35. T. Thaler P. Knochel Angew. Chem., Int. Ed. 2009 48 645
36. S. R. Harutyunyan T. den Hartog K. Geurts A. J. Minnaard B. L. Feringa Chem. Rev. 2008 108 2824
37. A. Alexakis J. E. Bäckvall N. Krause O. Pàmies M. Diéguez Chem. Rev. 2008 108 2796
38. S. R. Harutyunyan F. López W. R. Browne A. Correa D. Peña R. Badorrey A. Meetsma A. J. Minnaard B. L. Feringa J. Am. Chem. Soc. 2006 128 9103
39. S. H. Bertz S. Cope M. Murphy C. A. Ogle B. Taylor J. Am. Chem. Soc. 2007 129 7208
40. M. Shibasaki M. Kanai Chem. Rev. 2008 108 2853
41. D. Tomita M. Kanai M. Shibasaki Chem.-Asian J. 2006 1 161
42. D. Tomita R. Wada M. Kanai M. Shibasaki J. Am. Chem. Soc. 2005 127 4138
43. F. He Y. Bo J. D. Altom E. J. Corey J. Am. Chem. Soc. 1999 121 6771
44. S. A. Snyder A. Gollner M. I. Chiriac Nature 2011 474 461
45. A. Funayama T. Satoh M. Miura J. Am. Chem. Soc. 2005 127 15354
46. J. Siewert R. Sandmann P. von Zezschwitz Angew. Chem., Int. Ed. 2007 46 7122
47. W. P. Gallagher I. Terstiege R. E. Maleczka Jr. J. Am. Chem. Soc. 2001 123 3194
48. J. Yang C. Wang X. Xie H. Li E. Li Y. Li Org. Biomol. Chem. 2011 9 1342
49. S.-M. Lu C. Bolm Angew. Chem., Int. Ed. 2008 47 8920
50. R. Moser Z. V. Boskovic C. S. Crowe B. H. Lipshutz J. Am. Chem. Soc. 2010 132 7852