Enantioselection in asymmetric catalysis by Ilya D. Gridnev, Pavel A. Dub

By Ilya D. Gridnev, Pavel A. Dub

The box of uneven catalysis is at present one of many most popular components in chemistry. This exact booklet makes a speciality of the mechanism of enantioselectivity in uneven catalysis, instead of uneven catalysis from the unreal view. It describes trustworthy, experimentally and computationally supported mechanisms, and discusses the chance of so-called "plausible" or "accepted" mechanisms resulting in mistaken conclusions. It attracts parallels to enzymatic catalysis in biochemistry, and examines intimately the physico-chemical features of enantioselective catalysis.

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By Ilya D. Gridnev, Pavel A. Dub

The box of uneven catalysis is at present one of many most popular components in chemistry. This exact booklet makes a speciality of the mechanism of enantioselectivity in uneven catalysis, instead of uneven catalysis from the unreal view. It describes trustworthy, experimentally and computationally supported mechanisms, and discusses the chance of so-called "plausible" or "accepted" mechanisms resulting in mistaken conclusions. It attracts parallels to enzymatic catalysis in biochemistry, and examines intimately the physico-chemical features of enantioselective catalysis.

Show description

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Extra resources for Enantioselection in asymmetric catalysis

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Reprinted with permission from Gridnev, I. D. , 4, 203–219. ) the stabilities of the transition states for the double bond coordination TS11 and TS13; DG2, difference in the stabilities of the transition states for the oxidative addition of H2 TS15 and TS17; DG3, difference in the stabilities of the stereodetermining transition states for dihydride and unsaturated mechanisms. 2. 2). 2 kcal/mol less stable than the transition state of the double bond coordination. This value only slightly decreases at 173 K, hence the unsaturated pathway is not interfering with the dihydride route in this case at any temperature.

37,38 It is clear that, if the complete reversal of the sense of enantioselection was observed, such cases must exist that the competition between the alternative pathways would lead to the low optical yields. 5 31P NMR spectra (162 MHz, −90°C, CD3OD) of the reaction mixtures containing monohydride intermediate 92: (b) unlabeled: (a) labeled with 13C at the methylene carbon atom. Additional large coupling observed in the case of the labeled compound proves that 92 has a structure of b-monohydride.

31 Double bond coordination and migratory insertion steps in the nonchelating dihydride complexes 105a and 105b. (Reprinted with permission from Gridnev, I. , J. Am. Chem. , 130, 2560–2572. 8 Pathways for the double bond coordination and migratory insertion steps in the nonchelating complexes 105a and 105b computed on the B3LYP/SDD level of theory. (Reprinted with permission from Gridnev, I. , J. Am. Chem. , 130, 2560–2572. ) scan proceeds via a single maximum at approximately 3 Å and results in the corresponding dihydride intermediate.

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