Journal ArticleDOI
A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition.
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TLDR
A C2-symmetric norbornadiene derivative was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to alpha,beta-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.Abstract:
As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to α,β-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.read more
Citations
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Journal ArticleDOI
Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents.
TL;DR: Achieving chemo-, regioand stereocontrol in both asymmetric conjugate addition (ACA) and asymmetric allylic alkylation (AAA), however, has proven to be challenging and has restricted the application of these transformations, in particular, to total synthesis.
Journal ArticleDOI
Chiral olefins as steering ligands in asymmetric catalysis.
TL;DR: This work highlights the increasing number of chiral chelating olefin ligands as well as their application in a variety of metal-catalyzed transformations.
Journal ArticleDOI
Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): catalytic, kinetic resolution of allyl carbonates.
TL;DR: An Ir(I)-catalyzed kinetic resolution of secondary allylic carbonates allows for their isolation in up to 98% ee, and documents the synthesis and use of a new class of chiral [ 2.2.2]-bicyclooctadiene ligands for iridium.
Journal ArticleDOI
C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines
Norihito Tokunaga,Yusuke Otomaru,Kazuhiro Okamoto,Kazuhito Ueyama,Ryo Shintani,Tamio Hayashi +5 more
TL;DR: Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C2-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo(Ph-bod*) for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines
Journal ArticleDOI
Rhodium-Catalyzed Asymmetric Arylation
TL;DR: The research on these distinct families of chiral ligands are highlighted and their applications in the RCAA of arylmetals to activated alkenes, aldehydes, ketones and imines, and RCAA-tandem reactions are described.
References
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Journal ArticleDOI
Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II): an effective catalyst for cross-coupling of secondary and primary alkyl Grignard and alkylzinc reagents with organic halides
TL;DR: Etude d'une trentaine de reactions, avec des complexes de Ni au Pd pour le couplage des bromo-benzene, -styrene, -anisole, -toluene avec le chlorure de butylmagnesium as discussed by the authors.
Journal ArticleDOI
Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones
Journal ArticleDOI
Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium Intermediates
TL;DR: The catalytic cycle of asymmetric 1,4-addition of phenylboronic acid to an alpha,beta-unsaturated ketone catalyzed by a rhodium-binap complex was established by use of RhPh(PPh(3))(binap) as a key intermediate.
Journal ArticleDOI
Asymmetric conjugate 1,4-addition of arylboronic acids to alpha, beta-unsaturated esters catalyzed by Rhodium(I)/(S)-binap
TL;DR: The rhodium/(S)-binap complex provided (R)-3-phenylbutanoate in the addition of phenylboronic acid to benzyl crotonate and the effects on the enantioselectivity of chiral phosphine ligands, r Rhodium precursors, and substituents on alpha,beta-unsaturated esters are discussed.
Journal ArticleDOI
Rhodium-Catalyzed 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds: Large Accelerating Effects of Bases and Ligands
TL;DR: In this article, the effects of ligands and bases in the rhodium(I)-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds were reinvestigated to carry out the reaction under mild conditions.
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