Double-asymmetric hydrogenation strategy for the reduction of 1,1-diaryl olefins applied to an improved synthesis of CuIPhEt, a C2-symmetric N-heterocyclic carbenoid

Journal of Organic Chemistry

Volumn 78, Issue 6, 2013, Pages 2731-2735

  Spahn, Elizabeth ^a   Albright, Abigail ^a   Shevlin, Michael ^b   Pauli, Larissa ^c   Pfaltz, Andreas ^c   Gawley, Robert E ^a  

^a UNIVERSITY OF ARKANSAS   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CARBENOIDS; IMIDAZOLIUM; N-HETEROCYCLIC; P-TOLUIDINE; PHENYLACETYLENES; SELECTIVE HYDROGENATION;

HYDROGENATION; HYDROSILYLATION; OLEFINS; ORGANIC POLYMERS; PHOSPHORUS COMPOUNDS;

CATALYST SELECTIVITY;

ALKENE; CARBENOID; IRIDIUM; PHENYLACETYLENE; PHOSPHINE; RHODIUM; TOLUIDINE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYST; ENANTIOMER; HYDROGENATION; SYNTHESIS;

ALKENES; ALKYNES; ANILINE COMPOUNDS; CATALYSIS; COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; HYDROGENATION; MOLECULAR STRUCTURE; STEREOISOMERISM; TOLUIDINES;

EID: 84875152372     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3026548     Document Type: Article

References (29)

1. N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer-Verlag: Berlin, 2004; Vol. 21.
2. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006.
3. Díez-González; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
4. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
5. N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer: Berlin, 2007.
6. N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; Diez-Gonzalez, S., Ed.; Royal Society of Chemistry: London, 2010.
7. Kühl, O. Functionalized N-Heterocyclic Carbene Complexes; Wiley: New York, 2010.
8. N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis; Cazin, C. S. J., Ed.; Springer: Berlin, 2011.
9. Kaur, H.; Zinn, R. K.; Nolan, S. P. Organometallics 2004, 23, 1157
10. Albright, A.; Eddings, D.; Black, R.; Welch, C. J.; Gerasimchuk, N. N.; Gawley, R. E. J. Org. Chem. 2011, 76, 7341
11. Albright, A.; Gawley, R. E. J. Am. Chem. Soc. 2011, 133, 19680
12. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, G.; Tarantola, F. Tetrahedron 1997, 53, 3795
13. Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272
14. Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402
15. Church, T. L.; Andersson, P. G. Coord. Chem. Rev. 2008, 252, 513
16. Woodmansee, D. H.; Pfaltz, A. Chem. Commun. 2011, 47, 7912
17. Conticello, V. P.; Brard, L.; Giardello, M. A.; Tsuji, Y.; Sabat, M.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 2761
18. Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241
19. Blankenstein, J.; Pfaltz, A. Angew. Chem., Int. Ed. 2001, 40, 4445
20. McIntyre, S.; Hörmann, E.; Menges, F.; Smidt, S. P.; Pfaltz, A. Adv. Synth. Catal. 2005, 347, 282
21. Mazuela, J.; Verendel, J. J.; Coll, M.; Schäffner, B.; Börner, A.; Andersson, P. G.; Pàmies, O.; Diéguez, M. J. Am. Chem. Soc. 2009, 131, 12344
22. Knowles, W. S. Angew. Chem., Int. Ed. 2002, 41, 1998
23. Wang, X.; Guram, A.; Caille, S.; Hu, J.; Preston, J. P.; Ronk, M.; Walker, S. Org. Lett. 2011, 13, 1881
24. Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 2005, 646
25. Kaiser, S.; Smidt, S. P.; Pfaltz, A. Angew. Chem., Int. Ed. 2006, 45, 5194
26. Smidt, S. P.; Menges, F.; Pfaltz, A. Org. Lett. 2004, 6, 2023
27. Schrems, M. G.; Pfaltz, A. Chem. Commun. 2009, 0, 6210
28. Menges, F. University of Basel, 2004, http://edoc.unibas.ch/diss/DissB- 6766.
29. Zigterman, J. L.; Woo, J. C. S.; Walker, S. D.; Tedrow, J. S.; Borths, C. J.; Bunel, E. E.; Faul, M. M. J. Org. Chem. 2007, 72, 8870