Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

Chemical Science

Volumn 7, Issue 12, 2016, Pages 6919-6927

  Robinson, Emily R T ^a   Walden, Daniel M ^b   Fallan, Charlene ^a   Greenhalgh, Mark D ^a   Cheong, Paul Ha Yeon ^b   Smith, Andrew D ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; THIOUREAS;

BENZAZOLES; BENZOTHIAZOLES; BENZOXAZOLE DERIVATIVES; CHEMO-SELECTIVITY; HETEROCYCLES; ISOTHIOUREA; STRUCTURAL PREORGANIZATION;

CATALYSIS;

EID: 84995687647     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c6sc00940a     Document Type: Article

References (88)

1. R. Dua S. Shrivastava S. K. Sonwane S. K. Srivastava Adv. Biol. Res. 2011 5 120-144
2. T. Eicher and S.Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, Wiley-VCH, Weinheim, Germany, 2nd edn, 2003
3. R. S. Keri M. R. Patil S. A. Patil S. Budagumpi Eur. J. Med. Chem. 2015 89 207-251
4. S. Noel S. Cadet E. Gras C. Hureau Chem. Soc. Rev. 2013 42 7747-7762
5. Y. Bansal O. Silakari Bioorg. Med. Chem. 2012 20 6208-6236
6. C. S. Demmer L. Bunch Eur. J. Med. Chem. 2014 97 778-785
7. J. Kuwabara T. Namekawa M.-A. Haga T. Kanbara Dalton Trans. 2012 41 44-46
8. C. Zhang S.-B. Yu X.-P. Hu D.-Y. Wang Z. Zheng Org. Lett. 2010 12 5542-5545
9. B. Wang S. Wang C. Xia W. Sun Chem.-Eur. J. 2012 18 7332-7335
10. F. S. Rodembusch F. P. Leusin L. F. da Costa Medina A. Brandelli V. Stefani Photochem. Photobiol. Sci. 2005 4 254-259
11. For selected recent examples, see:
12. Q. Cai Z. Li J. Wei L. Fu C. Ha D. Pei K. Ding Org. Lett. 2010 12 1500-1503
13. H. De Silva S. Chatterjee W. P. Henry C. U. Pittman Jr Synthesis 2012 44 3453-3464
14. L. M. Stanley J. F. Hartwig J. Am. Chem. Soc. 2009 131 8971-8983
15. L. Li B.-A. Song P. S. Bhadury Y.-P. Zhang D.-Y. Hu S. Yang Eur. J. Org. Chem. 2011 2011 4743-4746
16. H.-X. He W. Yang D.-M. Du Adv. Synth. Catal. 2013 355 1137-1148
17. K. Xu N. Thieme B. Breit Angew. Chem., Int. Ed. 2014 53 2162-2165
18. H.-X. He D.-M. Du Eur. J. Org. Chem. 2014 2014 6190-6199
19. C. Fallan H. W. Lam Chem.-Eur. J. 2013 18 11214-11218
20. For seminal work on isothiourea catalysis see:
21. V. B. Birman X. Li Org. Lett. 2006 8 1351-1354
22. V. B. Birman H. Jiang X. Li L. Guo E. W. Uffman J. Am. Chem. Soc. 2006 128 6536-6537
23. M. Kobayashi S. Okamoto Tetrahedron Lett. 2006 47 4347-4350
24. V. B. Birman X. Li Org. Lett. 2008 10 1115-1118
25. Y. Zhang V. B. Birman Adv. Synth. Catal. 2009 351 2525-2529
26. C. Joannesse C. P. Johnston C. Concellón C. Simal D. Philp A. D. Smith Angew. Chem., Int. Ed. 2009 48 8914-8918
27. . For recent reviews, see:
28. L. C. Morrill A. D. Smith Chem. Soc. Rev. 2014 43 6214-6226
29. J. E. Taylor S. D. Bull J. M. J. Williams Chem. Soc. Rev. 2012 41 2109-2121
30. For selected examples see
31. D. Belmessieri L. C. Morrill C. Simal A. M. Z. Slawin A. D. Smith J. Am. Chem. Soc. 2011 133 2710-2714
32. D. Belmessieri D. B. Cordes A. M. Z. Slawin A. D. Smith Org. Lett. 2013 15 3472-3475
33. D. G. Stark L. C. Morrill P.-P. Yeh A. M. Z. Slawin T. J. C. O'Riordan A. D. Smith Angew. Chem., Int. Ed. 2013 52 11642-11646
34. S. R. Smith C. Fallan J. E. Taylor R. McLennan D. S. B. Daniels L. C. Morrill A. M. Z. Slawin A. D. Smith Chem.-Eur. J. 2015 21 10530-10536
35. E. R. T. Robinson C. Fallan C. Simal A. M. Z. Slawin A. D. Smith Chem. Sci. 2013 4 2193-2200
36. ; for other examples of related work using α,β-unsaturated acyl ammonium intermediates, see:
37. E. Bappert P. Müller G. C. Fu Chem. Commun. 2006 2604-2606
38. S. Vellalath K. N. Van D. Romo Angew. Chem., Int. Ed. 2013 52 13688-13693
39. G. Liu M. E. Shirley K. N. Van R. L. McFarlin D. Romo Nat. Chem. 2013 5 1049-1057
40. S. Goudedranche X. Bugaut T. Constantieux D. Bonne J. Rodriguez Chem.-Eur. J. 2014 20 410-415
41. Y. Fukata T. Omamura K. Asano S. Matsubara Org. Lett. 2014 16 2184-2187
42. Y. Fukata K. Asano S. Matsubara J. Am. Chem. Soc. 2015 137 5320-5323
43. For a recent review of related work using α,β-unsaturated acyl azolium intermediates, see:
44. L. Candish Y. Nakano D. W. Lupton Synthesis 2014 46 1823-1835
45. B. R. Beno K.-S. Yeung M. D. Bartberger L. D. Pennington N. A. Meanwell J. Med. Chem. 2015 58 4383-4438
46. R. C. Reid M.-K. Yau R. Singh J. Lim D. P. Fairlie J. Am. Chem. Soc. 2014 136 11914-11917
47. F. T. Burling B. M. Goldstein J. Am. Chem. Soc. 1992 114 2313-2320
48. For the initial postulate of 1,5-S⋯O interactions as a control element in isothiourea catalysis see
49. V. B. Birman X. Li Z. Han Org. Lett. 2007 9 37-40
50. . For other manuscripts of interest see
51. M. E. Abbasov B. M. Hudson D. J. Tantillo D. Romo J. Am. Chem. Soc. 2014 136 4492-4495
52. P. Liu X. Yang V. B. Birman K. N. Houk Org. Lett. 2012 14 3288-3291
53. C-H interactions disfavor alternative conformations with an O-C-N-C dihedral angle of 180°. See ref. 13b
54. See leading publications in ref. 12 and 13 and the following for a selection of discussions:
55. X. Zhang Z. Gong J. Li T. Lu J. Chem. Inf. Model. 2015 55 2138-2153
56. J. G. Angyan Á. Kucsman R. A. Poirier I. G. Csizmadia J. Mol. Struct.: THEOCHEM 1985 123 189-201
57. J. S. Murray P. Lane P. Politzer Int. J. Quantum Chem. 2008 108 2770-2781
58. M. Iwaoka S. Takemoto S. Tomoda J. Am. Chem. Soc. 2002 124 10613-10620
59. K. A. Brameld B. Kuhn D. C. Reuter M. Stahl J. Chem. Inf. Model. 2008 48 1-24
60. For selected reviews, see:
61. A. G. Doyle E. N. Jacobsen Chem. Rev. 2007 107 5713-5743
62. P. R. Schreiner Chem. Soc. Rev. 2003 32 289-296
63. The absolute configurations of all products are based upon previous reports of annulations using α,β-unsaturated acyl ammonium intermediates (see ref. 10 and 11)
64. −1. See ESI for further details
65. The corresponding acid (E : Z ratio 89 : 11) was prepared following a literature procedure (
66. P. Tarrant R. E. Taylor J. Org. Chem. 1959 24 1888-1890
67. ). The anhydride was prepared from this mixture, presumably as a statistical ratio of stereoisomers, and used without purification (see ESI for further information)
68. Y. Zhao D. G. Truhlar Theor. Chem. Acc. 2008 120 215-241
69. P. C. Hariharan J. A. Pople Theor. Chim. Acta 1973 28 213-222
70. W. J. Hehre R. Ditchfield J. A. Pople J. Chem. Phys. 1972 56 2257-2261
71. S. Miertuš E. Scrocco J. Tomasi Chem. Phys. 1981 55 117-129
72. See ESI for full authorship of Gaussian09:
73. M. J. Frisch, et al., Gaussian 09, Gaussian, Inc.: Wallingford, CT, 2009
74. E. Gould D. M. Walden K. Kasten R. C. Johnston J. Wu A. M. Z. Slawin T. J. L. Mustard B. Johnston T. Davies P. H.-Y. Cheong A. D. Smith Chem. Sci. 2014 5 3651-3658
75. M. Walker A. J. A. Harvey A. Sen C. E. H. Dessent J. Phys. Chem. A 2013 117 12590-12600
76. See ESI for reaction coordinates, intermediate and transition structures, model systems, and energetics
77. S. Alverez Dalton Trans. 2013 42 8617-8636
78. −1
79. D. M. Walden O. M. Ogba R. C. Johnston P. H.-Y. Cheong Acc. Chem. Res. 2016 49 1279-1291
80. P. Maity R. P. Pemberton D. J. Tantillo U. K. Tambar J. Am. Chem. Soc. 2013 135 16380-16383
81. O. Pattawong T. J. L. Mustard R. C. Johnston P. H.-Y. Cheong Angew. Chem., Int. Ed. 2013 52 1420-1423
82. R. C. Johnston P. H.-Y. Cheong Org. Biomol. Chem. 2013 11 5057-5064
83. M. N. Paddon-Row C. D. Anderson K. N. Houk J. Org. Chem. 2009 74 861-868
84. E. J. Corey J. J. Rohde Tetrahedron Lett. 1997 38 37-40
85. S. Wheeler Acc. Chem. Res. 2013 46 1029-1038
86. E. H. Krenske K. N. Houk Acc. Chem. Res. 2013 46 979-989
87. M. O. Sinnokrot E. F. Valeev C. D. Sherrill J. Am. Chem. Soc. 2002 124 10887-10893
88. C. Y. Legault, CYLview, 1.0b, Université de Sherbrooke, 2009