Literature DB >> 27548761

An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones.

Xiaohong Huo1, Rui He1, Xiao Zhang1, Wanbin Zhang1.   

Abstract

An Ir/Zn dual catalysis has been developed for the enantio- and diastereodivergent α-allylation of unprotected α-hydroxyketones under mild conditions, in the absence of any additional base. The cooperative action of a chiral iridium complex derived from phosphoramidites and a chiral Zn-ProPhenol complex is most likely responsible for its high reactivity, excellent enantioselectivity (up to >99% ee), and good diastereoselectivity (up to >20:1 dr). All four product stereoisomers could be prepared from the same set of starting materials and under identical conditions by simple selection of appropriate catalyst combinations.

Entities:  

Year:  2016        PMID: 27548761     DOI: 10.1021/jacs.6b06156

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

1.  Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.

Authors:  Xingyu Jiang; Philip Boehm; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-17       Impact factor: 15.419

2.  Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

Authors:  Wei Liu; Siraj Z Ali; Stephen E Ammann; M Christina White
Journal:  J Am Chem Soc       Date:  2018-08-17       Impact factor: 15.419

3.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

4.  Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-28       Impact factor: 15.336

Review 5.  Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors:  Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

6.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

7.  Remote Allylation of Unactivated C(sp3)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Authors:  Bin Xu; Uttam K Tambar
Journal:  ACS Catal       Date:  2019-04-16       Impact factor: 13.084

8.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

9.  Streamlined Catalytic Enantioselective Synthesis of α-Substituted β,γ-Unsaturated Ketones and Either of the Corresponding Tertiary Homoallylic Alcohol Diastereomers.

Authors:  Juan Del Pozo; Shaochen Zhang; Filippo Romiti; Shibo Xu; Ryan P Conger; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

10.  Evidence for an enolate mechanism in the asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts.

Authors:  Nariyoshi Umekubo; Takahiro Terunuma; Eunsang Kwon; Yujiro Hayashi
Journal:  Chem Sci       Date:  2020-09-21       Impact factor: 9.825

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