Literature DB >> 30582688

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions.

Qiang Cheng1, Hang-Fei Tu1, Chao Zheng1, Jian-Ping Qu2, Günter Helmchen3, Shu-Li You1.   

Abstract

In this review, we summarize the origin and advancements of iridium-catalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymmetric allylic substitution reactions have attracted intense attention due to their exceptionally high regio- and enantioselectivities. Ir-catalyzed asymmetric allylic substitution reactions have been significantly developed in recent years in many respects, including ligand development, mechanistic understanding, substrate scope, and application in the synthesis of complex functional molecules. In this review, an explicit outline of ligands, mechanism, scope of nucleophiles, and applications is presented.

Entities:  

Year:  2018        PMID: 30582688     DOI: 10.1021/acs.chemrev.8b00506

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  37 in total

1.  Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.

Authors:  Bin Xu; Ludovic Troian-Gautier; Ryan Dykstra; Robert T Martin; Osvaldo Gutierrez; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2020-03-19       Impact factor: 15.419

2.  Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation.

Authors:  Matteo Faltracco; Verena Sukowski; Max van Druenen; Trevor A Hamlin; F Matthias Bickelhaupt; Eelco Ruijter
Journal:  J Org Chem       Date:  2020-07-13       Impact factor: 4.354

3.  Regio- and Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines.

Authors:  Woo-Ok Jung; Minjin Yoo; Madyson M Migliozzi; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Org Lett       Date:  2021-12-14       Impact factor: 6.005

4.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors:  Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

5.  CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Authors:  Sheng Feng; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-24       Impact factor: 15.419

6.  Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis.

Authors:  Alexander W Schuppe; James Levi Knippel; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-30       Impact factor: 15.419

7.  Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Authors:  Colton R Davis; Irungu K Luvaga; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2021-03-23       Impact factor: 15.419

Review 8.  Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts.

Authors:  Lars Süsse; Brian M Stoltz
Journal:  Chem Rev       Date:  2021-02-11       Impact factor: 60.622

9.  Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer.

Authors:  Chao Sun; Xiaotian Qi; Xiao-Long Min; Xue-Dan Bai; Peng Liu; Ying He
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

10.  Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement.

Authors:  Xi-Shang Sun; Xing-Heng Wang; Hai-Yan Tao; Liang Wei; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2020-09-17       Impact factor: 9.825

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