Journal ArticleDOI
Atroposelective Synthesis of Axially Chiral Biaryl Compounds
Gerhard Bringmann,Anne J. Price Mortimer,Paul A. Keller,Mary J. Gresser,James Garner,Matthias Breuning +5 more
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TLDR
A review of axially chirality in biaryl compounds can be found in this paper, where the asymmetric information is introduced into a preformed, but achiral-that is, symmetric or configurationally labile-biaryl compound.Abstract:
A rotationally hindered and thus stereogenic biaryl axis is the structurally and stereochemically decisive element of a steadily growing number of natural products, chiral auxiliaries, and catalysts. Thus, it is not surprising that significant advances have been made in the asymmetric synthesis of axially chiral biaryl compounds over the past decade. In addition to the classic approach (direct stereoselective aryl-aryl coupling), innovative concepts have been developed in which the asymmetric information is introduced into a preformed, but achiral-that is, symmetric or configurationally labile-biaryl compound, or in which an aryl--C single bond is stereoselectively transformed into an axis. This Review classifies these strategies according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications. Furthermore, the preconditions required for the existence of axial chirality in biaryl compounds are discussed.read more
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Yong-Bin Wang,Bin Tan +1 more
TL;DR: The asymmetric organocatalytic approach to construct axially chiral styrenes through the 1,4-addition of arylalkynals in good chemical yields and enantioselectivities is discovered and the azo group can effectively perform as a directing and activating group for organoc atalytic formal aRYl C-H functionalization via formal nucleophilic aromatic substitution of azobenzene derivatives.
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Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations
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Journal ArticleDOI
Atroposelective Synthesis of Axially Chiral Biaryl Compounds
Gerhard Bringmann,Anne J. Price Mortimer,Paul A. Keller,Mary J. Gresser,James Garner,Matthias Breuning +5 more
TL;DR: This Review classifies strategies in the asymmetric synthesis of axially chiral biaryl compounds according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications.