(S)-Proline-derived new chiral ligands with phosphino, organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating element

Palladium‐Catalyzed Suzuki–Miyaura Reaction Involving a Secondary sp3 Carbon: Studies of Stereochemistry and Scope of the Reaction

“…Chiral sulfoxides have been used, for example, as chiral ligands in the asymmetric allylation of aldehydes [26] or in the asymmetric Trost reaction. [27] Sulfides similar to those expected from simple reduction of (S S ,R)-4'h are known to form palladacycles and might find applications in asymmetric Heck reactions. [28] From the perspective of sulfoxide chemistry, our route to (S S ,R)-4'h offers better results than alternative methods such as methylation of chiral benzyl p-tolyl sulfoxide, which always affords a mixture of diastereomers that are difficult to separate.…”

Organoselenium(II) and selenium(IV) compounds containing 2-(Me2NCH2)C6H4 moieties: solution behavior and solid state structure

“…In particular, for Se compounds derived from N,N-diorganobenzylamine and related ligands in which the nitrogen atom of the pendant arm is able to establish internal SeÁ Á ÁN interactions, the recent advances are due to their potential applications, e.g. for asymmetric synthesis in organic and organometallic chemistry [2][3][4][5][6][7][8][9][10][11], catalytic antioxidant activity, enzyme mimics and chemotherapeutic agents [12][13][14][15][16]. It was shown that such internal interactions play an important role in chirality transfer in asymmetric reactions.…”

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

“…[41] Uenishi has reported the P,N ligands 102 ± 107 and applied them in the allylic alkylation reaction where the results obtained gave insight into which structural features of the ligands are essential for high enantioselection, Table 7, entries 1 ± 10. [42] Both ent-102 and 106 gave lower enantioselection than 102 indicating, firstly, that there is a co-operative effect between the chiral centres in 102, and secondly, that it is the pyrrolidine chiral centre which is the major influence on the enantioselection.…”

“…These were applied to the asymmetric hydroboration of styrenes where 434 gave good enantioselectivity ( > 80%) for a range of substrates. [158] In the palladium-catalysed allylic alkylation of 1,3-diphenyl-2-propenyl acetate (15) those ligands with electron-withdrawing groups on the phosphorus were found to give the best enantioselection, Table 41. [159] The first ever axially chiral phosphinamine ligand, 1-(2'-diphenylphosphino-3',6'-dimethoxyphenyl)isoquinoline (440), was reported by Brown and Woodward in 1992.…”