Noncovalent Interactions in Organocatalysis and the Prospect of Computational Catalyst Design

Accounts of Chemical Research

Volumn 49, Issue 5, 2016, Pages 1061-1069

  Wheeler, Steven E ^a   Seguin, Trevor J ^a   Guan, Yanfei ^a   Doney, Analise C ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84969821604     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00096     Document Type: Article

References (49)

1. Copeland, G. T.; Miller, S. J. Selection of Enantioselective Acyl Transfer Catalysts from a Pooled Peptide Library through a Fluorescence-Based Activity Assay: An Approach to Kinetic Resolution of Secondary Alcohols of Broad Structural Scope J. Am. Chem. Soc. 2001, 123, 6496-6502 10.1021/ja0108584
2. Knowles, R. R.; Jacobsen, E. N. Attractive Noncovalent Interactions in Asymmetric Catalysis: Links between Enzymes and Small Molecule Catalysts Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20678-20685 10.1073/pnas.1006402107
3. Grimme, S. Density Functional Theory with London Dispersion Corrections WIREs Comp. Mol. Sci. 2011, 1, 211-228 10.1002/wcms.30
4. Ehrlich, S.; Moellmann, J.; Grimme, S. Dispersion-Corrected Density Functional Theory for Aromatic Interactions in Complex Systems Acc. Chem. Res. 2013, 46, 916-926 10.1021/ar3000844
5. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167 10.1021/ar700111a
6. Krenske, E. H.; Houk, K. N. Aromatic Interactions as Control Elements in Stereoselective Organic Reactions Acc. Chem. Res. 2013, 46, 979-989 10.1021/ar3000794
7. Wagner, J. P.; Schreiner, P. R. London Dispersion in Molecular Chemistry-Reconsidering Steric Effects Angew. Chem., Int. Ed. 2015, 54, 12274-12296 10.1002/anie.201503476
8. Raju, R. K.; Bloom, J. W. G.; An, Y.; Wheeler, S. E. Substituent Effects in Non-Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry ChemPhysChem 2011, 12, 3116-3130 10.1002/cphc.201100542
9. Wheeler, S. E. Understanding Substituent Effects in Non-Covalent Interactions Involving Aromatic Rings Acc. Chem. Res. 2013, 46, 1029-1038 10.1021/ar300109n
10. Wheeler, S. E.; Bloom, J. W. G. Toward a More Complete Understanding of Non-Covalent Interactions Involving Aromatic Rings J. Phys. Chem. A 2014, 118, 6133-6147 10.1021/jp504415p
11. Lu, T.; Zhu, R.; An, Y.; Wheeler, S. E. Origin of Enantioselectivity in the Propargylation of Aromatic Aldehydes Catalyzed by Helical N-Oxides J. Am. Chem. Soc. 2012, 134, 3095-3102 10.1021/ja209241n
12. Chen, J.; Captain, B.; Takenaka, N. Helical Chiral 2,2′-Bipyridine N-Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane Org. Lett. 2011, 13, 1654-1657 10.1021/ol200102c
13. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799 10.1002/jcc.20495
14. Rooks, B. J.; Haas, M. R.; Sepúlveda, D.; Lu, T.; Wheeler, S. E. Prospects for the Computational Design of Bipyridine N,N′-Dioxide Catalysts for Asymmetric Propargylations ACS Catal. 2015, 5, 272-280 10.1021/cs5012553
15. Salonen, L. M.; Ellermann, M.; Diederich, F. Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures Angew. Chem., Int. Ed. 2011, 50, 4808-4842 10.1002/anie.201007560
16. Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates Chem. Rev. 2014, 114, 9047-9153 10.1021/cr5001496
17. Neel, A. J.; Hehn, J. P.; Tripet, P. F.; Toste, F. D. Asymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids J. Am. Chem. Soc. 2013, 135, 14044-14047 10.1021/ja407410b
18. Sunoj, R. B. Transition State Models for Understanding the Origin of Chiral Induction in Asymmetric Catalysis. Acc. Chem. Res. 2016, DOI: 10.1021/acs.accounts.6b00053.
19. Jindal, G.; Sunoj, R. B. Axially Chiral Imidodiphosphoric Acid Catalyst for Asymmetric Sulfoxidation Reaction: Insights on Asymmetric Induction Angew. Chem., Int. Ed. 2014, 53, 4432-4436 10.1002/anie.201309532
20. Kötzner, L.; Martínez, A.; De Fusco, C.; List, B. Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes Angew. Chem., Int. Ed. 2014, 53, 5202-5205 10.1002/anie.201400474
21. Seguin, T. J.; Lu, T.; Wheeler, S. E. Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π-Stacking and CH/π Interactions Org. Lett. 2015, 17, 3066-3069 10.1021/acs.orglett.5b01349
22. Müller, S.; Webber, M. J.; List, B. The Catalytic Asymmetric Fischer Indolization J. Am. Chem. Soc. 2011, 133, 18534-18437 10.1021/ja2092163
23. Li, G.-Q.; Gao, H.; Keene, C.; Devonas, M.; Ess, D. H.; Kürti, L. Organocatalytic Aryl-Aryl Bond Formation: An Atroposelective [3,3]-Rearrangement Approach to BINAM Derivatives J. Am. Chem. Soc. 2013, 135, 7414-7417 10.1021/ja401709k
24. Seguin, T. J.; Wheeler, S. E. Electrostatic Basis of Asymmetric Ring Openings of meso-Epoxides ACS Catal. 2016, 6, 2681-2688 10.1021/acscatal.6b00538
25. Wang, Z.; Law, W. K.; Sun, J. Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of meso-Epoxides by Thiols Org. Lett. 2013, 15, 5964-5966 10.1021/ol402797v
26. Monaco, M. R.; Prévost, S.; List, B. Catalytic Asymmetric Synthesis of Thiols J. Am. Chem. Soc. 2014, 136, 16982-16985 10.1021/ja510069w
27. Monaco, M. R.; Prévost, S.; List, B. Organocatalytic Asymmetric Hydrolysis of Epoxides Angew. Chem., Int. Ed. 2014, 53, 8142-8145 10.1002/anie.201400170
28. Johnston, R. C.; Cohen, D. T.; Eichman, C. C.; Scheidt, K. A.; Cheong, P. H.-Y. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis Chem. Sci. 2014, 5, 1974-1982 10.1039/c4sc00317a
29. Houk, K. N.; Cheong, P. H.-Y. Computational Prediction of Small-Molecule Catalysts Nature 2008, 455, 309-313 10.1038/nature07368
30. Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Celebi-Olçüm, N.; Houk, K. N. Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities Chem. Rev. 2011, 111, 5042-5137 10.1021/cr100212h
31. Shinisha, C. B.; Janardanan, D.; Sunoj, R. B. Design of Catalysts for Aymmetric Organic Reactions through Density Functional Calculations. In Challenges and Advances in Computational Chemistry and Physics, Leszczynski, J., Ed.; Springer: New York, 2010.
32. Sunoj, R. B. Proline-Derived Organocatalysis and Synergism between Theory and Experiments WIREs Comp. Mol. Sci. 2011, 1, 920-931 10.1002/wcms.37
33. Rooks, B. J.; Wheeler, S. E. AARON, Automated Alkylation Reaction Optimizer for N-oxides, version 0.72; Texas A&M University: College Station, TX, 2015.
34. Guan, Y.; Rooks, B. J.; Wheeler, S. E. AARON: An Automated Reaction Optimizer for Non-metal catalyzed reactions, version 0.91; Texas A&M University: College Station, TX, 2016.
35. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. Asymmetric Allylation of Aldehydes with Chiral Lewis Bases J. Org. Chem. 1994, 59, 6161-6163 10.1021/jo00100a013
36. Denmark, S. E.; Fu, J. On the Mechanism of Catalytic, Enantioselective Allylation of Aldehydes with Chlorosilanes and Chiral Lewis Bases J. Am. Chem. Soc. 2000, 122, 12021-12022 10.1021/ja002060a
37. Denmark, S. E.; Wynn, T. Lewis Base Activation of Lewis Acids: Catalytic Enantioselective Allylation and Propargylation of Aldehydes J. Am. Chem. Soc. 2001, 123, 6199-6200 10.1021/ja016017e
38. Denmark, S. E.; Fu, J. Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones Chem. Rev. 2003, 103, 2763-2794 10.1021/cr020050h
39. Denmark, S. E.; Beutner, G. L. Lewis Base Catalysis in Organic Synthesis Angew. Chem., Int. Ed. 2008, 47, 1560-1638 10.1002/anie.200604943
40. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. (S)-3,3′-Dimethyl-2,2′-biquinoline N,N′-Dioxide as an Efficient Catalyst for Enantioselective Addition of Allyltrichlorosilanes to Aldehydes J. Am. Chem. Soc. 1998, 120, 6419-6420 10.1021/ja981091r
41. Nakajima, M.; Saito, M.; Hashimoto, S. Selective Synthesis of Optically Active Allenic and Homopropargylic Alcohols from Propargyl Chloride Tetrahedron: Asymmetry 2002, 13, 2449-2452 10.1016/S0957-4166(02)00640-7
42. Malkov, A. V.; Bell, M.; Orsini, M.; Pernazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Kočovský, P. New Lewis-Basic N-Oxides as Chiral Organocatalysts in Asymmetric Allylation of Aldehydes J. Org. Chem. 2003, 68, 9659-9668 10.1021/jo035074i
43. Malkov, A. V.; Ramirez-Lopez, P.; Biedermannova, L.; Rulisek, L.; Dufková, L.; Kotora, M.; Zhu, F.; Kočovky, P. On the Mechanism of Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by QUINOX, a Chiral Isoquinoline N-Oxide J. Am. Chem. Soc. 2008, 130, 5341-5348 10.1021/ja711338q
44. Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovsky, P. Chiral 2,2′-Bipyridine-Type N-Monoxides as Organocatalysts in the Enantioselective Allylation of Aldehydes with Allyltrichlorosilane Org. Lett. 2002, 4, 1047-1049 10.1021/ol025654m
45. Lu, T.; Porterfield, M. A.; Wheeler, S. E. Explaining the Disparate Stereoselectivities of N-Oxide Catalyzed Allylation and Propargylation of Aromatic Aldehydes Org. Lett. 2012, 14, 5310-5313 10.1021/ol302493d
46. Sepúlveda, D.; Lu, T.; Wheeler, S. E. Performance of DFT Methods and Origin of Stereoselectivity in Bipyridine N,N′-Dioxide Catalyzed Allylation and Propargylation Reactions Org. Biomol. Chem. 2014, 12, 8346-8353 10.1039/C4OB01719F
47. Wang, S.-G.; Liu, X.-J.; Zhao, Q.-C.; Zheng, C.; Wang, S.-B.; You, S.-L. Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction Angew. Chem., Int. Ed. 2015, 54, 14929-14932 10.1002/anie.201507998
48. Grimme, S. Supramolecular Binding Thermodynamics by Dispersion-Corrected Density Functional Theory Chem.-Eur. J. 2012, 18, 9955-9964 10.1002/chem.201200497
49. Burés, J.; Armstrong, A.; Blackmond, D. G. Explaining Anomalies in Enamine Catalysis: Downstream Species as a New Paradigm for Stereocontrol Acc. Chem. Res. 2016, 49, 214-222 10.1021/acs.accounts.5b00394