@article {32712, title = {Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity}, journal = {Chemistry {\textendash} A European Journal}, volume = {23}, year = {2017}, pages = {14248-14260}, abstract = {
Abstract Choosing the optimal catalyst for a new transformation is challenging because the ideal molecular requirements of the catalyst for one reaction do not always simply translate to another. Large groups at the 3,3\′ positions of the binaphthol rings are important for efficient stereoinduction but if they are too large this can lead to unusual or poor results. By applying a quantitative steric assessment of the substituents at the 3,3\′ positions of the binaphthol ring, we have systematically studied the effect of modulating this group on enantioselectivity for a wide range of reactions involving imines, and verified this analysis using ONIOM calculations. We have shown that in most reactions, the stereochemical outcome depends on both proximal and remote sterics. Summarising detailed calculations into a simple qualitative model identifies and explains the steric features required for high selectivity. This model is consistent with seventy seven papers reporting reactions (over 1000 transformations in total), and provides a straightforward decision tree for selecting the best catalyst.
}, keywords = {ASYMMETRIC CATALYSIS, binaphthol, catalyst choice, chirality, phosphoric acid}, doi = {10.1002/chem.201702019}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201702019}, author = {Reid, Jolene P. and Goodman, Jonathan M.} } @article {1527, title = {A simple, catalytic H-2-hydrogenation method for the synthesis of fine chemicals; hydrogenation of protoporphyrin IX dimethyl ester}, journal = {Tetrahedron Letters}, volume = {47}, number = {29}, year = {2006}, note = {ISI Document Delivery No.: 058XJTimes Cited: 2Cited Reference Count: 61Reboucas, Julio S. James, Brian R.}, month = {Jul}, pages = {5119-5122}, type = {Article}, abstract = {A conceptually simple H-2-hydrogenation protocol is introduced for the high-yield preparation of a natural product derivative. Protoporphyrin IX dimethyl ester is hydrogenated to the mesoporphyrin analogue in N,N-dimethylacetamide under H-2 (1 atm) at 80 degrees C within 30 min. The reaction is catalyzed by commercial RUCl3, without the need for the use of phosphine- and/or carbene-based ligands. (c) 2006 Elsevier Ltd. All rights reserved.}, keywords = {ASYMMETRIC CATALYSIS, CARBON-MONOXIDE, COMPLEXES, HEME OXYGENASE-1, HORSERADISH-PEROXIDASE, MESOPORPHYRIN, METALLOPORPHYRINS, NUCLEAR-MAGNETIC-RESONANCE, PORPHYRIN, RUTHENIUM(II) MYOGLOBIN}, isbn = {0040-4039}, url = {