Brown, John M. and Deeth, Robert J.. (2009) Is enantioselectivity predictable in asymmetric catalysis? Angewandte Chemie International Edition, Vol.48 (No.25). pp. 4476-4479. ISSN 1433-7851

Full text not available from this repository.

Abstract

A range of computational methods have been applied to harmonize predicted ee values with experimental values. Novel ways of combining quantum mechanics and molecular mechanics feature prominently.

[error in script] [error in script]

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Enantioselective catalysis, Asymmetric synthesis, Chemistry -- Data processing
Journal or Publication Title:	Angewandte Chemie International Edition
Publisher:	Wiley - V C H Verlag GmbH & Co. KGaA
ISSN:	1433-7851
Date:	2009
Volume:	Vol.48
Number:	No.25
Number of Pages:	4
Page Range:	pp. 4476-4479
Identification Number:	10.1002/anie.200900697
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Leverhulme Foundation
References:	[1] J. J. Burbaum, R. T. Raines, W. J. Albery, J. R. Knowles, Biochemistry 1989, 28, 9293 – 9305. [2] E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, CA, 2006, p. 358. [3] H. Lin, D. G. Truhlar, Theor. Chem. Acc. 2007, 117, 185 – 199. [4] a) IMOMM: F. Maseras, K. Morokuma, J. Comput. Chem. 1995, 16, 1170 – 1179; b) ONIOM: T. Vreven, K. S. Byun, I. Komaromi, S. Dapprich, J. A. Montgomery, K. Morokuma, M. J. Frisch, J. Chem. Theory Comput. 2006, 2, 815 – 826. [5] K. N. Houk, P. H. Y. Cheong, Nature 2008, 455, 309 – 313. [6] C. R. Corbeil, S. Thielges, J. A. Schwartzentruber, N. Moitessier, Angew. Chem. 2008, 120, 2675 – 2678; Angew. Chem. Int. Ed. 2008, 47, 2635 – 2638; ACE is asymmetric-catalyst evaluation. [7] a) D. Balcells, F. Maseras, New J. Chem. 2007, 31, 333 – 343; b) C. Bo, F. Maseras, Dalton Trans. 2008, 2911 – 2919. [8] M. Yamakawa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 6327 – 6335. [9] T. Rasmussen, P.-O. Norrby, J. Am. Chem. Soc. 2003, 125, 5130 – 5138. [10] Based on 3D-QSAR approaches to ligand-substrate interactions: A. Bender, J. L. Jenkins,Q. Li, S. E. Adams, E. O. Cannon, R. C. Glen, Annu. Rep. Comput. Chem. 2006, 2, 141 – 168. [11] a) J. C. Ianni, V. Annamalai, P.-W. Phuan, M. Panda, M. C. Kozlowski, Angew. Chem. 2006, 118, 5628 – 5631; Angew. Chem. Int. Ed. 2006, 45, 5502 – 5505; b) M. C. Kozlowski, S. L. Dixon, M. Panda, G. Lauri, J. Am. Chem. Soc. 2003, 125, 6614 – 6615; c) J. Huang, J. C. Ianni, J. E. Antoline, R. P. Hsung, M. C. Kozlowski, Org. Lett. 2006, 8, 1565 – 1568. [12] M. Urbano-Cuadrado, J. J. Carbo, A. G. Maldonado, C. Bo, J. Chem. Inf. Model. 2007, 47, 2228 – 2234. [13] J. M. Brown, Handbook of Homogeneous Hydrogenation, Vol. 3, Wiley-VCH, Weinheim, 2007, pp. 1073 – 1103; J. M. Brown, Compr. Asymmetric Catal. I–III, Vol. 1, Springer, Heidelberg, 1999, pp. 121 – 182. [14] I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183 – 7194, and references therein. [15] a) S. Feldgus, C. R. Landis, J. Am. Chem. Soc. 2000, 122, 12714- 12727; b) C. R. Landis, S. Feldgus, Angew. Chem. 2000, 112, 2985 – 2988; Angew. Chem. Int. Ed. 2000, 39, 2863 – 2866; c) S. Feldgus, C. R. Landis, Catal. Met. Complexes 2002, 25, 107 – 135. [16] M. Li, D. Tang, X. Luo, W. Shen, Int. J. Quantum Chem. 2005, 102, 53 – 63 (migratory insertion as turnover-limiting step (TLS) in case of structurally simple P-chirogenic diphosphines); I. D. Gridnev, T. Imamoto, G. Hoge, M. Kouchi, H. Takahashi, J. Am. Chem. Soc. 2008, 130, 2560 – 2572 (alkene reassociation as TLS in case of tBu2PCH2PtBuMe). [17] a) P. J. Donoghue, P. Helquist, O. Wiest, J. Org. Chem. 2007, 72, 839 – 847; b) P. J. Donoghue, P. Helquist, P.-O. Norrby, O. Wiest, J. Chem. Theory Comput. 2008, 4, 1313 – 1323; c) P. J. Donoghue, P. Helquist, P.-O. Norrby, O. Wiest, J. Am. Chem. Soc. 2009, 131, 410 – 411. [18] See for example: M. Alame, N. Pestre, C. de Bellefon, Adv. Synth. Catal. 2008, 350, 898 – 908. [19] D. Seebach, U. Groselj, D. M. Badine, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2008, 91, 1999 – 2034; we thank a referee for suggesting this reference. [20] Note added in proof (April 9, 2009): Comparison of computational methods for rhodium-catalyzed asymmetric hydrogenation with a range of C1-symmetric flexible phosphinophosphinite ligands showed that experimental ee values were best reproduced by full DFT treatment: S. M. A. Donald, A. Vidal-Ferran, F. Maseras, Can. J. Chem. 2009, 87, in press. We thank F.M. for a copy.
URI:	http://wrap.warwick.ac.uk/id/eprint/27736

Data sourced from Thomson Reuters' Web of Knowledge

Request changes to a record

Actions (login required)

View Item