Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity

Organic Letters

Volumn 18, Issue 13, 2016, Pages 3214-3217

  Lehnherr, Dan ^a   Ford, David D ^a   Bendelsmith, Andrew J ^a   Rose Kennedy, C ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIOUREA;

CATALYSIS; CHEMISTRY; HYDROGEN BOND; SOLUTION AND SOLUBILITY; STEREOISOMERISM;

CATALYSIS; HYDROGEN BONDING; SOLUTIONS; STEREOISOMERISM; THIOUREA;

EID: 84977262887     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b01435     Document Type: Article

References (27)

1. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296 10.1039/b107298f
2. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299-4306 10.1039/b511216h
3. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743 10.1021/cr068373r
4. Knowles, R. R.; Jacobsen, E. N. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20678-20685 10.1073/pnas.1006402107
5. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187-1198 10.1039/b801793j
6. Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534-561 10.1002/anie.201205449
7. Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603-614 10.1038/nchem.1405
8. Beckendorf, S.; Asmus, S.; Mancheno, O. G. ChemCatChem 2012, 4, 926-936 10.1002/cctc.201200134
9. Seidel, D. Synlett 2014, 25, 783-794 10.1055/s-0033-1340618
10. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198-7199 10.1021/ja801514m
11. Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030-5032 10.1021/ja101256v
12. Birrell, J. A.; Desrosiers, J.-N.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 13872-13875 10.1021/ja205602j
13. Lin, S.; Jacobsen, E. N. Nat. Chem. 2012, 4, 817-824 10.1038/nchem.1450
14. Bergonzini, G.; Schindler, C. S.; Wallentin, C.-J.; Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112-116 10.1039/C3SC52265B
15. Yeung, C. S.; Ziegler, R. E.; Porco, J. A., Jr.; Jacobsen, E. N. J. Am. Chem. Soc. 2014, 136, 13614-13617 10.1021/ja508523g
16. Liu, R. Y.; Wasa, M.; Jacobsen, E. N. Tetrahedron Lett. 2015, 56, 3428-3430 10.1016/j.tetlet.2015.01.124
17. Ford, D. D.; Lehnherr, D.; Kennedy, C. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 10.1021/jacs.6b04686.
18. Ford, D. D.; Lehnherr, D.; Kennedy, C. R.; Jacobsen, E. N. ACS Catal. 2016, 10.1021/acscatal.6b01384.
19. Ford, D. D. The Role of Catalyst-Catalyst Interactions in Asymmetric Catalysis with (salen)Co(III) Complexes and H-Bond Donors. Ph.D. Thesis, Harvard University, 2013.
20. Frisch, M. J.; et al., Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009; See Supporting Information for full citation.
21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652 10.1063/1.464913
22. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789 10.1103/PhysRevB.37.785
23. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206 10.1016/0009-2614(89)87234-3
24. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269 10.1063/1.447079
25. For a discussion of syn-pentane interactions in hydrocarbon backbones, see: Hoffmann, R. W.; Stahl, M.; Schopfer, U.; Frenking, G. Chem.-Eur. J. 1998, 4, 559-566 10.1002/(SICI)1521-3765(19980416)4:4<559::AID-CHEM559>3.0.CO;2-T
26. Tan, H. K. S. J. Chem. Soc., Faraday Trans. 1994, 90, 3521-3525 10.1039/ft9949003521
27. Nogales, D. F.; Ma, J.-S.; Lightner, D. A. Tetrahedron 1993, 49, 2361-2372 10.1016/S0040-4020(01)86316-X