Silver-catalysed enantioselective addition of O-H and N-H bonds to allenes: A new model for stereoselectivity based on noncovalent interactions

Chemistry - A European Journal

Volumn 18, Issue 36, 2012, Pages 11317-11324

  Arbour, Jannine L ^a   Rzepa, Henry S ^a   Contreras García, Julia ^b   Adrio, Luis A ^a   Barreiro, Elena M ^a   Hii, King Kuok ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

allenes; asymmetric catalysis; computational chemistry; noncovalent interactions; stereoselectivity

Indexed keywords

ABSOLUTE CONFIGURATION; ALLENES; ANIONIC LIGANDS; ANOMERIC EFFECT; ASYMMETRIC CATALYSIS; CATALYSE; COMPUTATIONAL APPROACH; DENSITY GRADIENTS; DISPERSIVE FORCES; ENANTIOSELECTIVE ADDITION; FREE-ENERGY CALCULATIONS; INTRAMOLECULAR ADDITIONS; ISO SURFACE; NON-COVALENT INTERACTION; OPTICALLY ACTIVE; SILVER COMPLEXES; TETRA-HYDROFURAN; TRANSITION STATE;

CATALYSIS; COMPUTATIONAL CHEMISTRY; COMPUTATIONAL METHODS; ENANTIOMERS; ENANTIOSELECTIVITY; HYDROCARBONS; SILVER;

STEREOSELECTIVITY;

EID: 84861176961     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200547     Document Type: Article

References (43)

1. V. M. Arredondo, F. E. McDonald, T. J. Marks, Organometallics 1999, 18, 1949-1960
2. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12-21
3. X. H. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 7244-7245
4. T. Bai, S. M. Ma, G. C. Jia, Coord. Chem. Rev. 2009, 253, 423-448
5. C. J. Weiss, T. J. Marks, Dalton Trans. 2010, 39, 6576-6588.
6. J. M. Hoover, J. R. Petersen, J. H. Pikul, A. R. Johnson, Organometallics 2004, 23, 4614-4620
7. A. J. Hickman, L. D. Hughs, C. M. Jones, H. Li, J. E. Redford, S. J. Sobelman, J. A. Kouzelos, A. R. Johnson, Tetrahedron: Asymmetry 2009, 20, 1279-1285
8. K. E. Near, B. M. Chapin, D. C. McAnnally-Linz, A. R. Johnson, J. Organomet. Chem. 2011, 696, 81-86.
9. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499
10. R. L. LaLonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452-2453
11. Z. Zhang, C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2007, 129, 14148-14149
12. Z. B. Zhang, C. F. Bender, R. A. Widenhoefer, Org. Lett. 2007, 9, 2887-2889
13. Z. B. Zhang, R. A. Widenhoefer, Angew. Chem. 2007, 119, 287-289
14. Angew. Chem. Int. Ed. 2007, 46, 283-285
15. K. Aikawa, M. Kojima, K. Mikami, Angew. Chem. 2009, 121, 6189-6193
16. Angew. Chem. Int. Ed. 2009, 48, 6073-6077
17. K. Aikawa, M. Kojima, K. Mikami, Adv. Synth. Catal. 2010, 352, 3131-3135
18. R. L. LaLonde, Z. J. Wang, M. Mba, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608-611
19. Angew. Chem. Int. Ed. 2010, 49, 598-601
20. H. Li, S. Du Lee, R. A. Widenhoefer, J. Organomet. Chem. 2011, 696, 316-320.
21. N. D. Shapiro, V. Rauniyar, G. L. Hamilton, J. Wu, F. D. Toste, Nature 2011, 470, 245-249
22. L. Ackermann, A. Althammer, Synlett 2008, 995-998.
23. J. L. Arbour, H. S. Rzepa, A. J. P. White, K. K. Hii, Chem. Commun. 2009, 7125-7127.
24. D. Lathbury, T. Gallagher, J. Chem. Soc. Chem. Commun. 1986, 114-115
25. N. J. S. Huby, R. G. Kinsman, D. Lathbury, P. G. Vernon, T. Gallagher, J. Chem. Soc. Perkin Trans. 1 1991, 145-155.
26. For the recent use of chiral silver-phosphate complexes for the kinetic resolution of racemic allenic alcohols, see:, Y. Wang, K. Zheng, R. Hong, J. Am. Chem. Soc. 2012, 134, 4096-4099.
27. J. Hopewell, P. Jankowski, C. L. McMullin, A. G. Orpen, P. G. Pringle, Chem. Commun. 2010, 46, 100-102.
28. A. Voituriez, A. B. Charette, Adv. Synth. Catal. 2006, 348, 2363-2370.
29. J. G. Taylor, L. A. Adrio, K. K. Hii, Dalton Trans. 2010, 39, 1171-1175.
30. Triflic acid catalyses the cyclisation of compound 4 a in a 6-endo manner, see:, K. Mori, S. Sueoka, T. Akiyama, Chem. Lett. 2009, 38, 628-629.
31. J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615-6620.
32. F. Cherblanc, Y. P. Lo, E. De Gussem, L. Alcazar-Fuoli, E. Bignell, Y. He, N. Chapman-Rothe, P. Bultinck, W. A. Herrebout, R. Brown, H. S. Rzepa, M. J. Fuchter, Chem. Eur. J. 2011, 17, 11868-11875.
33. Y. K. Chung, G. C. Fu, Angew. Chem. 2009, 121, 2259-2261
34. Angew. Chem. Int. Ed. 2009, 48, 2225-2227.
35. For a review, see, L. A. Nafie, Nat. Prod. Commun. 2008, 3, 451-466.
36. V. P. Nicu, E. J. Baerends, Phys. Chem. Chem. Phys. 2009, 11, 6107-6118.
37. C. S. M. Allan, H. S. Rzepa, J. Chem. Theory Comput. 2008, 4, 1841-1848.
38. The absolute stereochemical assignments as reported in reference [3g] have since been reassigned:, K. Aikawa, M. Kojima, K. Mikami, Adv. Synth. Catal. 2011, 353, 2882.
39. H. S. Rzepa, Chem. Commun. 2011, 47, 1851-1853.
40. E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras- García, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498-6506.
41. J. Contreras-García, W. Yang, E. R. Johnson, J. Phys. Chem. A 2011, 115, 12983-12990.
42. Also see:, A. M. R. Smith, H. S. Rzepa, A. J. P. White, D. Billen, K. K. Hii, J. Org. Chem. 2010, 75, 3085-3096.
43. J. H. Downing, J. Floure, K. Heslop, M. F. Haddow, J. Hopewell, M. Lusi, H. Phetmung, A. G. Orpen, P. G. Pringle, R. I. Pugh, D. Zambrano-Williams, Organometallics 2008, 27, 3216-3224.