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

By Hélène Pellissier

The aim of this e-book is to teach the excessive capability of chiral sulfur-containing ligands to advertise a number of uneven catalytic changes. the real variety of studies seemed within the literature over the past 35 years usually highlighted miraculous ends up in phrases of potency and enantioselectivity, permitting entry to many biologically vital molecules, which truly demonstrates that those ligands can now be known as actual rivals to the extra traditional phosphorus- or nitrogen-containing ligands. A key element of reference for post-graduate scholars, researchers and teachers.

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60). 61). Almost no attention has been paid to diphosphine sulfides employed as chiral ligands for palladium-catalysed nucleophilic substitution reactions. In this context, enantiomerically pure diphosphine sulfides derived from 2,2 0 biphosphole, which combined axial chirality and phosphorus chiralities, were synthesised, in 2008, by Gouygou et al. 61 Test reaction with thiophene diamine ligands. 62 Test reaction with 2,2 0 -biphosphole-derived diphosphine sulfide. allowed an excellent yield and an enantioselectivity of 73% ee to be obtained.

16 R = i-Pr: 100% ee = 93% (S) R = Me: 91% ee = 61% (S) R = Ph: 90% ee = 47% (S) R = t-Bu: 48% ee = 95% (S) Test reaction with furanoside thioether-phosphite or -phosphinite ligands. 16). 16). In this case, the enantioselectivities were strongly dependent on the steric properties of the substituent in the thioether moiety of the carbohydrate backbone. 49 In all cases, the best enantioselectivity (up to 91% ee) was obtained by using the ligand that contained the more bulky sulfur substituent (t-Bu).

Almost no attention has been paid to diphosphine sulfides employed as chiral ligands for palladium-catalysed nucleophilic substitution reactions. In this context, enantiomerically pure diphosphine sulfides derived from 2,2 0 biphosphole, which combined axial chirality and phosphorus chiralities, were synthesised, in 2008, by Gouygou et al. 61 Test reaction with thiophene diamine ligands. 62 Test reaction with 2,2 0 -biphosphole-derived diphosphine sulfide. allowed an excellent yield and an enantioselectivity of 73% ee to be obtained.

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