A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes.
نویسندگان
چکیده
A 2,4,6-trialkylanilide-containing chiral diene has been identified as a superior ligand for the enantioselective rhodium-catalyzed arylation of alkenylazaarenes with arylboronic acids.
منابع مشابه
"Sulfolefin": a mixed sulfinamido-olefin ligand in enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones.
Performing catalytic enantioselective carbon-carbon bond forming reactions, especially for the synthesis of tertiary carbinols, is one of the most challenging goals in modern asymmetric synthesis. Herein, we report an efficient enantioselective catalytic approach for the 1,2-addition of arylboronic acids to trifluoromethyl ketones affording tertiary trifluoromethyl-substituted alcohols with hig...
متن کاملEnantioselective Rhodium‐Catalyzed Coupling of Arylboronic Acids, 1,3‐Enynes, and Imines by Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
A chiral rhodium complex catalyzes the highly enantioselective coupling of arylboronic acids, 1,3-enynes, and imines to give homoallylic sulfamates. The key step is the generation of allylrhodium(I) species by alkenyl-to-allyl 1,4-rhodium(I) migration.
متن کاملEnantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones.
The catalytic asymmetric 1,2-addition of a series of arylboronic acids to 2,2,2-trifluoroacetophenones is described with high isolated yields (up to 96%) and good enantioselectivities (up to 83% ee) using a rhodium(I)/phosphoramidite catalyst.
متن کاملRhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines.
Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched α-branched amines (up to 99 % ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimim...
متن کاملAn N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.
A new bidentate phosphoramidite (N-Me-BIPAM) based on Shibasaki's N-linked BINOL was synthesized. This ligand appears to be highly effective for rhodium-catalyzed asymmetric conjugated addition of arylboronic acids to α,β-unsaturated enones. The reaction of ortho-substituted arylboronic acid with acyclic and cyclic enones provides the corresponding products in good yields and enantioselectivities.
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ورودعنوان ژورنال:
- Chemical communications
دوره 50 22 شماره
صفحات -
تاریخ انتشار 2014