Axially chiral imidodiphosphoric acid catalyst for asymmetric sulfoxidation reaction: Insights on asymmetric induction

Angewandte Chemie - International Edition

Volumn 53, Issue 17, 2014, Pages 4432-4436

  Jindal, Garima ^a   Sunoj, Raghavan B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

asymmetric catalysis; Br nsted acids; density functional calculations; noncovalent interactions; transition states

Indexed keywords

DENSITY FUNCTIONAL THEORY; IONS;

ASYMMETRIC CATALYSIS; ASYMMETRIC INDUCTION; CHIRAL INDUCTION; NON-COVALENT INTERACTION; SINGLE OXYGEN ATOM; STEREOCONTROLLING; STERIC INTERACTIONS; TRANSITION STATE;

OXIDATION;

BISPHOSPHONIC ACID DERIVATIVE; IMIDODIPHOSPHONIC ACID; SULFOXIDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; DIPHOSPHONATES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFOXIDES;

EID: 84899019668     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309532     Document Type: Article

References (88)

1. Chiral drugs: Chemistry and biological action (Eds.:, G.-Q. Lin, Q.-D. You, J.-F. Cheng,), Wiley, Hoboken, 2011
2. H. Caner, E. Groner, L. Levy, I. Agranat, Drug Discovery Today 2004, 9, 105.
3. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691
4. A. Pfaltz, W. J. Drury ? III, Proc. Natl. Acad. Sci. USA 2004, 101, 5723.
5. S. Caron, R. W. Dugger, S. G. Ruggeri, J. A. Ragan, D. H. Brown?Ripin, Chem. Rev. 2006, 106, 2943.
6. P. Pitchen, E. Duñach, M. N. Deshmukh, H. B. Kagan, J. Am. Chem. Soc. 1984, 106, 8188
7. F. Di?Furia, G. Modena, R. Seraglia, Synthesis 1984, 325
8. E. Wojaczyńska, J. Wojaczyński, Chem. Rev. 2010, 110, 4303
9. I. Fernández, N. Khiar, Chem. Rev. 2003, 103, 3651
10. J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19
11. H. Srour, P. L. Maux, S. Chevance, G. Simonneaux, Coord. Chem. Rev. 2013, 257, 3030.
12. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133.
13. R. Bentley, Chem. Soc. Rev. 2005, 34, 609.
14. H. L. Holland, Chem. Rev. 1988, 88, 473
15. H. L. Holland, Nat. Prod. Rep. 2001, 18, 171.
16. K. A. Stingl, S. B. Tsogoeva, Tetrahedron: Asymmetry 2010, 21, 1055
17. F. Shi, M. K. Tse, H. M. Kaiser, M. Beller, Adv. Synth. Catal. 2007, 349, 2425
18. H. Firouzabadi, N. Iranpoor, A. A. Jafari, E. Riazymontazer, Adv. Synth. Catal. 2006, 348, 434
19. A. Russo, A. Lattanzi, Adv. Synth. Catal. 2009, 351, 521.
20. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
21. T. Akiyama, Chem. Rev. 2007, 107, 5744
22. M. Terada, Chem. Commun. 2008, 4097
23. A. Zamfir, S. Schenker, M. Freund, S. B. Tsogoeva, Org. Biomol. Chem. 2010, 8, 5262
24. W. Tang, X. Xhang, Chem. Rev. 2003, 103, 3029; for metal catalysis see
25. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603
26. M. Mahlau, B. List, Angew. Chem. 2013, 125, 540
27. Angew. Chem. Int. Ed. 2013, 52, 518
28. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496
29. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336; for computational studies see
30. L. Simõn, J. M. Goodman, J. Org. Chem. 2011, 76, 1775
31. L. Simõn, J. M. Goodman, J. Am. Chem. Soc. 2008, 130, 8741
32. T. Marcelli, P. Hammar, F. Himo, Adv. Synth. Catal. 2009, 351, 525
33. M. Terada, K. Soga, N. Momiyama, Angew. Chem. 2008, 120, 4190
34. Angew. Chem. Int. Ed. 2008, 47, 4122
35. S. Xu, Z. Wang, Y. Li, X. Zhang, H. Wang, K. Ding, Chem. Eur. J. 2010, 16, 3021.
36. S. Liao, I. Čoric̈, Q. Wang, B. List, J. Am. Chem. Soc. 2012, 134, 10765.
37. I. Čoric̈, B. List, Nature 2012, 483, 315
38. J. H. Kim, I. Čoric̈, S. Vellalath, B. List, Angew. Chem. 2013, 125, 4570
39. Angew. Chem. Int. Ed. 2013, 52, 4474
40. K. Wu, Y.-J. Jiang, Y.-S. Fan, D. Sha, S. Zhang, Chem. Eur. J. 2013, 19, 474.
41. D. Ajami, J. Rebek,? Jr., Acc. Chem. Res. 2013, 46, 990
42. J. Rebek,? Jr., Acc. Chem. Res. 2009, 42, 1660
43. M. R. Ams, D. Ajami, S. L. Craig, J.-S. Yang, J. Rebek,? Jr., J. Am. Chem. Soc. 2009, 131, 13190
44. R. Breslow, J. Biol. Chem. 2009, 284, 1337
45. H. Zhao, F. W. Foss,? Jr., J. Am. Chem. Soc. 2008, 130, 12590
46. C. E. Müller, D. Zell, R. Hrdina, R. C. Wende, L. Wanka, S. M. M. Schuler, P. R. Schreiner, J. Org. Chem. 2013, 78, 8465.
47. C. B. Shinisha, R. B. Sunoj, J. Am. Chem. Soc. 2010, 132, 12319
48. A. K. Sharma, R. B. Sunoj, Angew. Chem. 2010, 122, 6517
49. Angew. Chem. Int. Ed. 2010, 49, 6373
50. G. Jindal, R. B. Sunoj, Chem. Eur. J. 2012, 18, 7045
51. All calculations were done using Gaussian09. See the Supporting Information for full details
52. Gaussian 09 Revision A.02, Frisch, M.?J. et?al. Gaussian, Inc, Wallingford, CT, 2004.
53. L. Simõn, J. M. Goodman, Org. Biomol. Chem. 2011, 9, 689
54. H. Yang, M. W. Wong, J. Am. Chem. Soc. 2013, 135, 5808
55. D. A. DiRocco, E. L. Noey, K. N. Houk, T. Rovis, Angew. Chem. 2012, 124, 2441
56. Angew. Chem. Int. Ed. 2012, 51, 2391
57. L. Simõn, J. M. Goodman, J. Am. Chem. Soc. 2012, 134, 16869
58. optimization has been performed for all conformers at the B3LYP level of theory. Further, optimizations have been carried out at the B3LYP-D3 level to account for dispersion effects. See Tables?S3,S4 (for I) and S7,S8 (for III) in the Supporting Information
59. to view the 3D geometries of important TSs, See: http://www.chem.iitb.ac. in/sunoj/SI-Sulphoxidation/SI-Sulpho.html (Java script required to run). We thank an anonymous referee for suggesting the kinemage tool to generate the 3D images.
60. D. C. Richardson, J. S. Richardson, Protein Sci. 1992, 1, 3.
61. Sulfoxidation reactions in the absence of catalysts are known to proceed only at higher temperatures (ca. 75 C). See:, M. Jereb, Green Chem. 2012, 14, 3047.
62. IRC calculations and Wiberg indices clearly show the formation of SO bond and cleavage of OO bond take place simultaneously. See Figures?S3,S4 and Table?S9 of the Supporting Information
63. the BSSE corrected values are provided in the Supporting Information.
64. A thorough conformational sampling, consisting of as many as 48 unique transition states, is done to identify the most preferred stereocontrolling TSs. See Figure?S2 and Tables?S1-S4 for in the Supporting Information complete details.
65. M. N. Grayson, S. C. Pellegrinet, J. M. Goodman, J. Am. Chem. Soc. 2012, 134, 2716
66. I. Čoric̈, J. H. Kim, T. Vlaar, M. Patil, W. Thiel, B. List, Angew. Chem. 2013, 125, 3574
67. Angew. Chem. Int. Ed. 2013, 52, 3490
68. Comparison of the optimized geometries of the TSs is given in Figure?S5 of the Supporting Information.
69. R. F. Bader, Atoms in Molecules: A Quantum Theory, Clarendon, Oxford, 1990
70. AIM2000 Version 2.0; Buro fur Innovative Software, SBK-Software: Bielefeld, Germany, 2002.
71. Noncovalent interactions have been invoked to rationalize stereoselectivity in asymmetric organocatalytic reactions. See
72. E. H. Krenske, K. N. Houk, Acc. Chem. Res. 2013, 46, 979
73. R. R. Knowles, E. N. Jacobsen, Proc. Natl. Acad. Sci. USA 2010, 107, 20678
74. C. Uyeda, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 5062
75. M. C. Holland, S. Paul, W. B. Schweizer, K. Bergander, C. Mück-Lichtenfeld, S. Lakhdar, H. Mayr, R. Gilmour, Angew. Chem. 2013, 125, 8125
76. Angew. Chem. Int. Ed. 2013, 52, 7967
77. R. C. Johnston, P. H.-Y. Cheong, Org. Biomol. Chem. 2013, 11, 5057
78. S. E. Allen, J. Mahatthananchai, J. W. Bode, M. C. Kozlowski, J. Am. Chem. Soc. 2012, 134, 12098
79. see Ref.?[14b]
80. P. H.-Y. Cheong, C. Y. Legault, J. M. Um, N. Çelebi- Ölçüm, K. N. Houk, Chem. Rev. 2011, 111, 5042.
81. The entropic gain obtained through desolvation, as invoked in aqueous enzymatic reactions, is not expected to contribute here
82. we thank the anonymous referee for sharing this insightful view.
83. See computational methods for a description of the activation strain analysis
84. F. M. Bickelhaupt, J. Comput. Chem. 1999, 20, 114
85. A. Diefenbach, F. M. Bickelhaupt, J. Phys. Chem. A 2004, 108, 8460
86. C. Y. Legault, Y. Garcia, C. A. Merlic, K. N. Houk, J. Am. Chem. Soc. 2007, 129, 12664.
87. The PyMOL Molecular Graphics System, Version 1.2r3pre, Schrödinger, LLC
88. the increased distortion in TS III-si, as noted through the root mean square deviation (RMSD) values, can also be understood by comparing some pertinent geometric parameters as illustrated in Figure?S6.