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

By Hélène Pellissier

The target of this booklet is to teach the excessive power of chiral sulfur-containing ligands to advertise a number of uneven catalytic modifications. the real variety of stories seemed within the literature over the past 35 years frequently highlighted amazing ends up in phrases of potency and enantioselectivity, permitting entry to many biologically very important molecules, which in actual fact demonstrates that those ligands can now be recognized as genuine opponents to the extra traditional phosphorus- or nitrogen-containing ligands. A key aspect of reference for post-graduate scholars, researchers and lecturers.

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62 Test reaction with 2,2 0 -biphosphole-derived diphosphine sulfide. allowed an excellent yield and an enantioselectivity of 73% ee to be obtained. In order to gain insight into the coordination chemistry of these ligands towards palladium, these authors have prepared the corresponding diphosphine analogues.

41 N N Ph SPh SPh 59% ee = 48% 78% ee = 96% Test reaction with thioimidazoline ligands. 41. More recently, Kim et al. have reported the synthesis of analogous chiral imidazolidine ligands, such as thioimidazolidines starting from (R,R)-1,2-diaminocyclohexane. 42. In all cases, the reactions were performed in the presence of a ligand/catalyst ratio of 4/1. 81 Some new chiral oxazolidine-thioether and thiazolidine-methanol ligands have been efficiently synthesised by Braga et al. 43). Subtle changes in the ligand’s structure made it possible to clarify the mode of action, determine a ligand structure–catalyst efficiency relationship and undertake a rational improvement of the ligand’s structure.

Thus, a number of cyclic and acyclic aminothioethers as well as iminothioethers have been synthesised and successfully used in these reactions. ,19c have been the most studied. The ligands developed by Williams et al. 24 Test reaction with sulfanylmethyl-, aryl-, and thiophene-oxazoline ligands. thiophene ring, were prepared with good yields by reacting the appropriate nitriles with homochiral aminoalcohols in order to study the control of the stereochemical course of the reaction via the modified binding properties, electronic behaviour and steric environment of both the oxazoline and the sulfur group.

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