Literature DB >> 25904287

Recent advances and new concepts for the synthesis of axially stereoenriched biaryls.

J Wencel-Delord1, A Panossian, F R Leroux, F Colobert.   

Abstract

Axial chirality is a key feature of many important organic molecules, such as biologically active compounds, stereogenic ligands and optically pure materials. Significant efforts in the field of the atropisomeric synthesis of biaryls have hence been undertaken over the past decade. Several major improvements of the already known methods to build up such chiral backbones (e.g. oxidative couplings and stereoselective Suzuki-Miyaura arylations) have been achieved and, in parallel, novel concepts have emerged enabling unprecedented synthetic routes toward molecules of this kind. These outstanding steps further unlocked the door to the preparation of previously difficult-to-access precursors of privileged ligands like BINOL, BINAM, QUINAP and many other molecules of interest.

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Year:  2015        PMID: 25904287     DOI: 10.1039/c5cs00012b

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  40 in total

1.  Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.

Authors:  Jin-Zheng Wang; Jin Zhou; Chang Xu; Hongbin Sun; László Kürti; Qing-Long Xu
Journal:  J Am Chem Soc       Date:  2016-04-14       Impact factor: 15.419

2.  Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

Authors:  John D Jolliffe; Roly J Armstrong; Martin D Smith
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

3.  Chiral Brønsted Acid Catalyzed Kinetic Resolutions.

Authors:  Kimberly S Petersen
Journal:  Asian J Org Chem       Date:  2016-03-07       Impact factor: 3.319

4.  Organocatalytic asymmetric arylation of indoles enabled by azo groups.

Authors:  Liang-Wen Qi; Jian-Hui Mao; Jian Zhang; Bin Tan
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

5.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

6.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

7.  Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.

Authors:  Omar M Beleh; Edward Miller; F Dean Toste; Scott J Miller
Journal:  J Am Chem Soc       Date:  2020-09-14       Impact factor: 15.419

8.  Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2 -Symmetric Biaryls.

Authors:  Gavin Coombs; Marcus H Sak; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-30       Impact factor: 15.336

9.  Enantioselective synthesis of 3-arylquinazolin-4(3H)-ones via peptide-catalyzed atroposelective bromination.

Authors:  Matthew E Diener; Anthony J Metrano; Shuhei Kusano; Scott J Miller
Journal:  J Am Chem Soc       Date:  2015-09-18       Impact factor: 15.419

Review 10.  BIAN-NHC Ligands in Transition-Metal-Catalysis: A Perfect Union of Sterically Encumbered, Electronically Tunable N-Heterocyclic Carbenes?

Authors:  Changpeng Chen; Feng-Shou Liu; Michal Szostak
Journal:  Chemistry       Date:  2021-01-18       Impact factor: 5.236

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