Literature DB >> 26187028

Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Inji Shin1, Michael J Krische2.   

Abstract

Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C-H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

Entities:  

Keywords:  Allylation; Dehydrogenation; Diastereoselectivity; Enantioselectivity; Green chemistry; Iridium; Polyketides; Transfer hydrogenation

Mesh：

Substances：

Year:  2016        PMID： 26187028      PMCID： PMC4716893          DOI： 10.1007/128_2015_651

Source DB:  PubMed          Journal:  Top Curr Chem        ISSN： 0340-1022


  68 in total

1.  Concise formal synthesis of (+)-neopeltolide.

Authors:  Zhen Yang; Bingbin Zhang; Gaoyuan Zhao; Juan Yang; Xingang Xie; Xuegong She
Journal:  Org Lett       Date:  2011-10-13       Impact factor: 6.005

2.  Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

Authors:  Chad A Lewis; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-25       Impact factor: 15.336

3.  Protecting-group-free total syntheses: a challenging approach.

Authors:  Emmanuel Roulland
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

4.  Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.

Authors:  Thomas M Beale; Mark S Taylor
Journal:  Org Lett       Date:  2013-03-06       Impact factor: 6.005

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative.

Authors:  Lina Chan; Mark S Taylor
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

7.  Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs.

Authors:  Chad A Lewis; Janie Merkel; Scott J Miller
Journal:  Bioorg Med Chem Lett       Date:  2008-09-09       Impact factor: 2.823

8.  Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin.

Authors:  Sunkyu Han; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-08-07       Impact factor: 15.419

9.  Chemical tailoring of teicoplanin with site-selective reactions.

Authors:  Tejas P Pathak; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-05-21       Impact factor: 15.419

10.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419
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  13 in total

1.  Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

Authors:  Inji Shin; Suckchang Hong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

2.  Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

Authors:  James M Cabrera; Johannes Tauber; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

Review 3.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

4.  Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

5.  Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.

Authors:  Seung Wook Kim; Wonchul Lee; Michael J Krische
Journal:  Org Lett       Date:  2017-02-21       Impact factor: 6.005

Review 6.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

7.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

Review 8.  Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors:  Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

9.  Total Synthesis of (+)-SCH 351448: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis.

Authors:  Gang Wang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-06-23       Impact factor: 15.419

10.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419
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