OpenLB
Open Library of Bioscience
Advanced Search
Chemistry (Weinheim an der Bergstrasse, Germany)
Sep 17, 2010;16 (35): 10616-28.

Kinetic isotope effects in asymmetric reactions.

Thomas Giagou, Matthew P Meyer
Author Information
  1. Thomas Giagou: School of Natural Sciences, University of California, Merced, 5200 N. Lake Rd., Merced, CA 95344, USA.
PMID: 20669194 DOI: 10.1002/chem.201001018

Abstract

Kinetic isotope effects are exquisitely sensitive probes of transition structure. As such, kinetic isotope effects offer a uniquely useful probe for the symmetry-breaking process that is inherent to stereoselective reactions. In this Concept article, we explore the role of steric and electronic effects in stereocontrol, and we relate these concepts to recent studies carried out in our laboratory. We also explore the way in which kinetic isotope effects serve as useful points of contact with computational models of transition structures. Finally, we discuss future opportunities for kinetic isotope effects to play a role in asymmetric catalyst development.

References

  1. Org Lett. 2007 Dec 20;9(26):5481-4 [PMID: 18041844]
  2. Angew Chem Int Ed Engl. 2008;47(22):4208-10 [PMID: 18412199]
  3. Tetrahedron Lett. 2009 Dec 9;50(49):6803-6806 [PMID: 26989268]
  4. J Am Chem Soc. 2009 Oct 7;131(39):13963-71 [PMID: 19754046]
  5. J Am Chem Soc. 2009 Apr 8;131(13):4685-94 [PMID: 19292447]
  6. Angew Chem Int Ed Engl. 2010 Mar 8;49(11):2058-62 [PMID: 20175171]
  7. J Am Chem Soc. 2009 Nov 11;131(44):16002-3 [PMID: 19831346]
  8. Bioorg Med Chem Lett. 2009 Jul 15;19(14):3934-7 [PMID: 19362473]
  9. Chem Rev. 2006 Aug;106(8):3140-69 [PMID: 16895322]
  10. Acc Chem Res. 2004 Aug;37(8):558-69 [PMID: 15311955]
  11. J Am Chem Soc. 2009 Mar 11;131(9):3130-1 [PMID: 19215077]
  12. Angew Chem Int Ed Engl. 2006 Feb 27;45(10):1520-43 [PMID: 16491487]
  13. J Am Chem Soc. 2008 Nov 5;130(44):14544-55 [PMID: 18847260]
  14. Acc Chem Res. 2004 Aug;37(8):548-57 [PMID: 15311954]
  15. Org Lett. 2007 Apr 26;9(9):1663-5 [PMID: 17408276]
  16. Org Lett. 2009 Aug 20;11(16):3598-601 [PMID: 19627144]
  17. J Am Chem Soc. 2009 Feb 11;131(5):1632-3 [PMID: 19191687]
  18. J Chem Phys. 2007 Apr 14;126(14):144503 [PMID: 17444719]
  19. Org Lett. 2009 Oct 1;11(19):4338-41 [PMID: 19775183]
  20. J Am Chem Soc. 2008 Apr 30;130(17):5789-97 [PMID: 18393424]
  21. J Org Chem. 2009 Sep 4;74(17):6503-10 [PMID: 19670893]
  22. J Phys Chem A. 2008 Dec 4;112(48):12416-29 [PMID: 18989948]
  23. Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5138-75 [PMID: 15455437]
  24. J Phys Chem A. 2008 Jan 10;112(1):9-22 [PMID: 18069803]
  25. Angew Chem Int Ed Engl. 1975;14(6):417 [PMID: 808983]
  26. Angew Chem Int Ed Engl. 1998 Aug 17;37(15):1986-2012 [PMID: 29711061]
  27. J Org Chem. 2008 Jan 4;73(1):309-11 [PMID: 18052189]
  28. J Comput Chem. 2006 Nov 30;27(15):1787-99 [PMID: 16955487]
  29. J Am Chem Soc. 2007 Sep 5;129(35):10678-85 [PMID: 17691728]
  30. Chemistry. 2010 May 3;16(17):5148-62 [PMID: 20349469]
  31. J Am Chem Soc. 2006 Jun 14;128(23):7594-607 [PMID: 16756316]
  32. Angew Chem Int Ed Engl. 2003 May 25;42(20):2258-60 [PMID: 12772156]
  33. Biochemistry. 2010 Apr 13;49(14):3168-73 [PMID: 20225826]
  34. J Am Chem Soc. 2009 Jan 21;131(2):653-61 [PMID: 19093864]
  35. J Am Chem Soc. 2009 Oct 7;131(39):13952-62 [PMID: 19788330]
  36. Acc Chem Res. 2006 Feb;39(2):93-100 [PMID: 16489728]
  37. J Am Chem Soc. 2008 Dec 31;130(52):17632-3 [PMID: 19061319]
  38. J Am Chem Soc. 2010 Apr 28;132(16):5584-5 [PMID: 20355730]
  39. J Am Chem Soc. 2010 Apr 7;132(13):4534-5 [PMID: 20232913]
  40. J Am Chem Soc. 2008 Jun 25;130(25):7816-7 [PMID: 18517199]
  41. Angew Chem Int Ed Engl. 2008;47(4):771-4 [PMID: 18069711]
  42. J Org Chem. 2007 Oct 26;72(22):8434-51 [PMID: 17918998]
  43. J Am Chem Soc. 2008 Sep 3;130(35):11617-9 [PMID: 18693725]
  44. Org Lett. 2010 Feb 5;12(3):604-7 [PMID: 20043644]
  45. Chem Rev. 2007 Dec;107(12):5471-569 [PMID: 18072803]
  46. J Am Chem Soc. 2007 Jul 18;129(28):8781-93 [PMID: 17592842]
  47. Acc Chem Res. 2004 Aug;37(8):580-91 [PMID: 15311957]
  48. Biochemistry. 2008 Apr 1;47(13):4169-80 [PMID: 18321070]
  49. J Am Chem Soc. 2008 Feb 6;130(5):1583-91 [PMID: 18193866]
  50. J Am Chem Soc. 2009 Feb 18;131(6):2397-403 [PMID: 19146405]
  51. J Am Chem Soc. 2007 Jun 6;129(22):7055-64 [PMID: 17497857]
  52. J Am Chem Soc. 2010 Apr 7;132(13):4510-1 [PMID: 20232868]
  53. J Org Chem. 2009 Oct 16;74(20):7633-43 [PMID: 19813764]
  54. Org Biomol Chem. 2005 Mar 7;3(5):719-24 [PMID: 15731852]
  55. J Am Chem Soc. 1986 Apr 1;108(9):2353-7 [PMID: 22175583]
  56. J Org Chem. 2007 Aug 3;72(16):6183-9 [PMID: 17608437]
  57. Acc Chem Res. 2002 Jun;35(6):341-9 [PMID: 12069618]
  58. Chem Soc Rev. 2009 Aug;38(8):2178-89 [PMID: 19623342]
  59. Nature. 2006 Jun 1;441(7093):621-3 [PMID: 16738656]
  60. J Org Chem. 2008 Jul 4;73(13):4819-29 [PMID: 18533704]
  61. Angew Chem Int Ed Engl. 2007;46(25):4748-50 [PMID: 17503406]
  62. Biochemistry. 2008 Oct 21;47(42):11158-63 [PMID: 18817416]
  63. Chem Rev. 2006 Nov;106(11):4518-84 [PMID: 17091928]
  64. Angew Chem Int Ed Engl. 2004 Nov 5;43(43):5765-8 [PMID: 15484203]
  65. Org Lett. 2009 Oct 15;11(20):4584-7 [PMID: 19754074]
  66. J Phys Chem A. 2009 Dec 24;113(51):14161-9 [PMID: 19928891]
  67. J Am Chem Soc. 2009 Aug 26;131(33):11985-97 [PMID: 19618933]
  68. Chem Rev. 2007 Nov;107(11):5004-64 [PMID: 17999556]
  69. J Phys Chem A. 2006 Apr 20;110(15):5121-9 [PMID: 16610834]
  70. Angew Chem Int Ed Engl. 2010 May 10;49(21):3635-7 [PMID: 20394089]
  71. Chem Rev. 2006 Aug;106(8):3170-87 [PMID: 16895323]
  72. Angew Chem Int Ed Engl. 2008;47(30):5641-5 [PMID: 18567027]
  73. Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5839-42 [PMID: 15073330]
  74. Environ Sci Technol. 2008 Nov 1;42(21):7744-50 [PMID: 19031855]
  75. J Am Chem Soc. 2008 Dec 31;130(52):17858-66 [PMID: 19053445]
  76. J Am Chem Soc. 2007 Aug 22;129(33):10276-81 [PMID: 17655301]
  77. Chem Rev. 2005 Aug;105(8):2999-3093 [PMID: 16092826]
  78. Nat Chem Biol. 2010 Jun;6(6):405-7 [PMID: 20418878]
  79. J Am Chem Soc. 2003 Nov 12;125(45):13836-49 [PMID: 14599224]
  80. J Am Chem Soc. 2010 Apr 14;132(14):5114-20 [PMID: 20302299]
  81. Inorg Chem. 2010 Apr 19;49(8):3661-75 [PMID: 20380467]
  82. Angew Chem Int Ed Engl. 2009;48(9):1609-13 [PMID: 19156797]
  83. Chem Rev. 2006 Aug;106(8):3095-118 [PMID: 16895320]
  84. J Am Chem Soc. 2009 Jun 24;131(24):8382-3 [PMID: 19485324]
  85. J Phys Chem A. 2007 Nov 8;111(44):11287-93 [PMID: 17705351]
  86. Org Lett. 2010 Jun 18;12(12):2794-7 [PMID: 20486656]

Grants

  1. R15 GM087706/NIGMS NIH HHS
  2. R15 GM087706-01/NIGMS NIH HHS
  3. GM87706-01/NIGMS NIH HHS

MeSH Term

Boranes
Catalysis
Computers, Molecular
Isotopes
Kinetics
Models, Molecular
Stereoisomerism

Chemicals

Boranes
Isotopes
Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.
Article has an altmetric score of 3

Word Cloud

Created with Highcharts 10.0.0effectsisotopekineticKinetictransitionusefulreactionsexploreroleasymmetricexquisitelysensitiveprobesstructureofferuniquelyprobesymmetry-breakingprocessinherentstereoselectiveConceptarticlestericelectronicstereocontrolrelateconceptsrecentstudiescarriedlaboratoryalsowayservepointscontactcomputationalmodelsstructuresFinallydiscussfutureopportunitiesplaycatalystdevelopment

Similar Articles

Cited By