Electronic effects steer the mechanism of asymmetric hydrogenations of unfunctionalized aryl-substituted alkenes

Journal of the American Chemical Society

Volumn 126, Issue 51, 2004, Pages 16688-16689

  Fan, Yubo ^a   Cui, Xiuhua ^a   Burgess, Kevin ^a   Hall, Michael B ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DISSOCIATION; ELECTRONICS; ENANTIOSELECTIVITY; HYDROGENATION; REDUCTION; SUBSTITUTION REACTION;

EID: 11244340733     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044240g     Document Type: Article

References (12)

1. Crabtree, R. Acc. Chem. Res. 1979, 12, 331-337.
2. Lightfoot, A;. Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897-2899.
3. Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hormann, E.; McIntyre, S.; Menges, F.; Schonleber, M.; Smidt, S. P.; Wustenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33-43.
4. Drury, W. J., III; Zimmermann, N.; Keenan, M.; Hayashi, M.; Kaiser, S.; Goddard, R.; Pfaltz, A. Angew. Chem., Int. Ed. 2004, 43, 70-74.
5. Cozzi, P. G.; Menges, F.; Kaiser, S. Synlett 2003, 833-836.
6. Xu, G.; Gilbertson, S. Tetrahedron Lett. 2003, 44, 953-955.
7. Tang, W.; Wang, W.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 943-946.
8. Gaussian 03 was used to fully optimize all structures, and then frequencies were analytically computed at the same level to confirm they were minima or transition states, as appropriate. Thermodynamic functions were calculated at 298.15 K and 1 atm. In the B3LYP calculations, a modified LANL2DZ with one f-function was used for the iridium atom. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.04; Gaussian, Inc.: Wallingford, CT, 2004.
9. Powell, M. T.; Hou, D.-R.; Perry, M. C.; Cui, X.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 8878-8879.
10. Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 113-123.
11. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
12. Brandt, P.; Hedberg, C.; Andersson, P. Chem. - Eur. J. 2003, 9, 339-347.