Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions

Organic Letters

Volumn 14, Issue 9, 2012, Pages 2258-2261

  Tang, Wenjun ^a   Patel, Nitinchandra D ^b   Xu, Guangqing ^a   Xu, Xiaobing ^a   Savoie, Jolaine ^b   Ma, Shengli ^b   Hao, Ming Hong ^b   Keshipeddy, Santosh ^b   Capacci, Andrew G ^b   Wei, Xudong ^b   Zhang, Yongda ^b   Gao, Joe J ^b   Li, Wenjie ^b   Rodriguez, Sonia ^b   Lu, Bruce Z ^b   Yee, Nathan K ^b   Senanayake, Chris H ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZOLE DERIVATIVE; LIGAND; ORGANOPHOSPHORUS COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZOXAZOLES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; LIGANDS; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84860610835     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300659d     Document Type: Article

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37. Zhou, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289) and supplied by the Gaussian 03 package (MidiX) for the first-row atoms (H, C, N, and O). For phosphorus, the 6-31G(d) basis set was employed; for palladium, the all-electron basis set from optimization of fcc Pd bulk (http://www.chimifm. unito.it/teprica/crystal/crystal.html) was employed. The coordinates of the 24 unique energy-minimized conformations were observed. Three lowest-energy conformations were found with a relative energy of 0, 0.51, and 0.78 kcal/mol, respectively. All other conformations have energies >2 kcal/mol or higher than the lowest-energy state. There are two main interesting observations from the calculation results. First, all three lowest-energy conformations lead to the same chirality in the coupling product that is in agreement with the inferred axial chirality of 6d. This result suggests that the energetics of the nonbonded π-interaction of the aromatic systems indeed dictate the conformation of the transition state and the chirality of the product. Secondly, the origin of the π-stacking interaction in determining the energetics of this system is most clearly seen in the lowest and 2nd lowest-energy conformations. See Supporting Information for more details.