Literature DB >> 26671223

Iridium-Catalyzed C-C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation.

Tao Liang1, Wandi Zhang1, Michael J Krische1.   

Abstract

A chiral iridium complex formed in situ from [Ir(cod)Cl]2 and (R)-H8-BINAP is found to catalyze the direct enantioselective C-C coupling of a simple propargyl ether, TIPSOCH2C≡CH, with primary alcohols to form γ-hydroxy (Z)-enol silanes with uniformly high enantioselectivity and complete alkene (Z)-stereoselectivity. As corroborated by deuterium labeling studies, these studies represent the first examples of 1,2-hydride shift-enabled π-allyl formation in the context of iridium catalysis.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 26671223      PMCID： PMC4697880          DOI： 10.1021/jacs.5b12131

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


  21 in total

1.  Creation of quaternary stereocenters in carbonyl allylation reactions.

Authors:  Ilan Marek; Genia Sklute
Journal:  Chem Commun (Camb)       Date:  2006-12-06       Impact factor: 6.222

2.  Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

Authors:  Tomoya Miura; Yui Nishida; Masao Morimoto; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

3.  Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors:  Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal:  Chem Rev       Date:  2011-09-16       Impact factor: 60.622

4.  Chromium-catalyzed homoaldol equivalent reaction employing a nucleophilic propenyl acetate.

Authors:  Jun Yong Kang; Brian T Connell
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

5.  Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling.

Authors:  Tao Liang; Khoa D Nguyen; Wandi Zhang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-03-03       Impact factor: 15.419

6.  Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-13       Impact factor: 15.336

7.  Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors:  Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-09-29       Impact factor: 15.419

8.  Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-31       Impact factor: 15.336

9.  Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry.

Authors:  Tomoya Miura; Yui Nishida; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2014-04-22       Impact factor: 15.419

10.  Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition.

Authors:  Boyoung Y Park; Khoa D Nguyen; Mani Raj Chaulagain; Venukrishnan Komanduri; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-07-30       Impact factor: 15.419
View more
  13 in total

1.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

2.  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 3.  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

4.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

5.  Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl anti-(α-Aryl)allylation.

Authors:  Ming Xiang; Ankan Ghosh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

6.  Enantioselective Addition of α-Nitroesters to Alkynes.

Authors:  Ryan T Davison; Patrick D Parker; Xintong Hou; Crystal P Chung; Sara A Augustine; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-07       Impact factor: 15.336

7.  Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Authors:  Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-11       Impact factor: 16.383

8.  Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Benjamin M Partridge; Michael Callingham; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

9.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

10.  Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration.

Authors:  Yang Yang; Ian B Perry; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-08-01       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.