Chemistry

Chiral Sulfur Ligands: Asymmetric Catalysis (RSC Catalysis by Hélène Pellissier

By Hélène Pellissier

The objective of this ebook is to teach the excessive strength of chiral sulfur-containing ligands to advertise various uneven catalytic alterations. the real variety of stories seemed within the literature during the last 35 years usually highlighted extraordinary leads to phrases of potency and enantioselectivity, permitting entry to many biologically vital molecules, which basically demonstrates that those ligands can now be known as genuine rivals to the extra ordinary phosphorus- or nitrogen-containing ligands. A key aspect of reference for post-graduate scholars, researchers and teachers.

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Although a large variety of structurally diverse ligands have already been tested in asymmetric catalysis, the cyclopropane skeletons have received relatively little attention to date. In this context, Molander et al. 20 to have the optimal configuration for the test reaction. On the basis of X-ray crystallographic data and NMR studies, the absolute configuration of the products was explained by a nucleophilic attack occurring at the carbon trans to the p-accepting phosphorus atom. In 1995, Pregosin et al.

This observation of a difference in the behaviour among the chalconide donors provided evidence for the higher ability of selenium to complex with palladium, leading to a superior level of enantioselection (up to 98% ee). 45 Test reaction with b-thioamide ligands. 46 O solvent = DME: S p-Tol 18% ee = 50% Test reaction with amino sulfoxide ligands. The test reaction has also been studied by Hiroi et al. 46. 46. In a different context, Ba¨ckvall et al. 47 * + RMgX R = n-Bu, X = I: 100% ee = 42% R = n-Bu, X = Br: 92% ee = 30% R = i-Pr, X = I: 100% ee = 29% R = i-Bu, X = Br: 56% ee = 40% Arenethiolatocopper(I)-catalysed substitution reactions of RMgX with allylic substrates.

50). The positive effect of the steric hindrance arising from the tert-butyl group was demonstrated since no enantioselectivity was observed in the case of using the corresponding ligand that did not bear this substituent. 49 Pd SbF6Cy : 75% ee = 82% (S) S Test reaction with S/C ligands. 50 O S + PF6t-Bu Pd o-Tol Test reaction with P/N-sulfinyl-imine ligand. 91 The most selective ligand (R1 ¼ c-Pent, R2 ¼ Ph) of the series was also applied to the nucleophilic substitution reaction of 1,3-diphenyl-2-propenyl acetate with substituted malonates, such as acetamido-derived diethylmalonate, which provided the corresponding product in 89% yield and 98% ee.

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