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J Am Chem Soc. 2017 Mar 29;139(12):4366-4375. doi: 10.1021/jacs.6b11851. Epub 2017 Mar 10.

Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study.

Journal of the American Chemical Society

Thomas H West, Daniel M Walden, James E Taylor, Alexander C Brueckner, Ryne C Johnston, Paul Ha-Yeon Cheong, Guy C Lloyd-Jones, Andrew D Smith

Affiliations

  1. EaStCHEM, School of Chemistry, University of St Andrews , North Haugh, St. Andrews, KY16 9ST, U.K.
  2. Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97333, United States.
  3. EaStCHEM, School of Chemistry, University of Edinburgh , Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, U.K.

PMID: 28230365 PMCID: PMC5374492 DOI: 10.1021/jacs.6b11851

Abstract

A mechanistic study of the isothiourea-catalyzed enantioselective [2,3]-rearrangement of allylic ammonium ylides is described. Reaction kinetic analyses using

References

  1. J Am Chem Soc. 2005 Feb 2;127(4):1066-7 - PubMed
  2. J Am Chem Soc. 2005 Jul 6;127(26):9352-3 - PubMed
  3. J Am Chem Soc. 2006 Mar 15;128(10):3355-65 - PubMed
  4. J Am Chem Soc. 2006 Aug 2;128(30):9722-9 - PubMed
  5. Org Lett. 2006 Oct 12;8(21):4859-61 - PubMed
  6. Org Lett. 2007 Jan 4;9(1):37-40 - PubMed
  7. J Org Chem. 2007 Feb 16;72(4):1294-300 - PubMed
  8. J Am Chem Soc. 2007 Apr 11;129(14):4490-7 - PubMed
  9. J Am Chem Soc. 2008 Feb 27;130(8):2378-9 - PubMed
  10. J Am Chem Soc. 2009 Feb 18;131(6):2397-403 - PubMed
  11. J Am Chem Soc. 2009 Mar 11;131(9):3126-7 - PubMed
  12. Chem Soc Rev. 2009 Apr;38(4):1027-38 - PubMed
  13. Angew Chem Int Ed Engl. 2011 Mar 7;50(11):2564-7 - PubMed
  14. Org Biomol Chem. 2011 Nov 7;9(21):7275-81 - PubMed
  15. J Am Chem Soc. 2011 Aug 24;133(33):12956-9 - PubMed
  16. Org Lett. 2011 Sep 16;13(18):4755-7 - PubMed
  17. Chem Soc Rev. 2012 Mar 21;41(6):2109-21 - PubMed
  18. Org Lett. 2012 Jul 6;14(13):3288-91 - PubMed
  19. Acc Chem Res. 2013 Apr 16;46(4):979-89 - PubMed
  20. Angew Chem Int Ed Engl. 2012 Sep 17;51(38):9638-42 - PubMed
  21. Molecules. 2013 Feb 18;18(2):2281-96 - PubMed
  22. Chem Rev. 2013 Oct 9;113(10):7851-79 - PubMed
  23. Org Lett. 2013 Sep 20;15(18):4770-3 - PubMed
  24. Org Lett. 2013 Oct 4;15(19):5138-41 - PubMed
  25. J Am Chem Soc. 2014 Mar 12;136(10):3740-3 - PubMed
  26. J Am Chem Soc. 2014 Mar 26;136(12):4492-5 - PubMed
  27. J Am Chem Soc. 2014 Mar 26;136(12):4476-9 - PubMed
  28. J Phys Chem A. 2014 Aug 14;118(32):6133-47 - PubMed
  29. J Am Chem Soc. 2014 Aug 27;136(34):11914-7 - PubMed
  30. J Am Chem Soc. 2015 Mar 25;137(11):3811-26 - PubMed
  31. J Med Chem. 2015 Jun 11;58(11):4383-438 - PubMed
  32. J Chem Inf Model. 2015 Oct 26;55(10):2138-53 - PubMed
  33. J Am Chem Soc. 2016 Jan 13;138(1):433-43 - PubMed
  34. J Am Chem Soc. 2016 Apr 6;138(13):4270-7 - PubMed
  35. Acc Chem Res. 2016 May 17;49(5):1019-28 - PubMed
  36. Acc Chem Res. 2016 May 17;49(5):1061-9 - PubMed
  37. Acc Chem Res. 2016 Jun 21;49(6):1279-91 - PubMed
  38. Angew Chem Int Ed Engl. 2016 Oct 4;55(41):12596-624 - PubMed
  39. ACS Cent Sci. 2016 Jun 22;2(6):416-23 - PubMed
  40. Nat Chem. 2016 Nov;8(11):1067-1075 - PubMed
  41. Chem Sci. 2016 Dec 1;7(12):6919-6927 - PubMed
  42. Chem Sci. 2015 Jul 1;6(7):3746-3756 - PubMed

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