Literature DB >> 23841678

Ruthenium catalyzed reductive coupling of paraformaldehyde to trifluoromethyl allenes: CF3-bearing all-carbon quaternary centers.

Brannon Sam1, T Patrick Montgomery, Michael J Krische.   

Abstract

Trifluoromethyl substituted allenes engage in ruthenium catalyzed reductive couplings with paraformaldehyde to form products of hydrohydroxymethylation as single regioisomers. This method enables generation of CF3-bearing all-carbon quaternary stereocenters.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23841678      PMCID： PMC3779475          DOI： 10.1021/ol401771a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

Review 1.  Analysis of the reactions used for the preparation of drug candidate molecules.

Authors:  John S Carey; David Laffan; Colin Thomson; Mike T Williams
Journal:  Org Biomol Chem       Date:  2006-05-03       Impact factor: 3.876

Review 2.  Asymmetric synthesis of active pharmaceutical ingredients.

Authors:  Vittorio Farina; Jonathan T Reeves; Chris H Senanayake; Jinhua J Song
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Applied hydroformylation.

Authors:  Robert Franke; Detlef Selent; Armin Börner
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

4.  Selective palladium-catalyzed hydroformylation of alkynes to α,β-unsaturated aldehydes.

Authors:  Xianjie Fang; Min Zhang; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-20       Impact factor: 15.336

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 rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehyes with diazaphospholane ligands.

Authors:  Avery L Watkins; Clark R Landis
Journal:  Org Lett       Date:  2010-12-06       Impact factor: 6.005

7.  Divergent regioselectivity in the synthesis of trisubstituted allylic alcohols by nickel- and ruthenium-catalyzed alkyne hydrohydroxymethylation with formaldehyde.

Authors:  Cory C Bausch; Ryan L Patman; Bernhard Breit; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-09       Impact factor: 15.336

8.  Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (α-trifluoromethyl)allylation from the alcohol or aldehyde oxidation level.

Authors:  Xin Gao; Yong Jian Zhang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-06       Impact factor: 15.336

9.  Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors.

Authors:  Helmut Werner; Ralf Wiedemann; Matthias Laubender; Bettina Windmüller; Paul Steinert; Olaf Gevert; Justin Wolf
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

10.  High stereoselective preparation of O-protected 2-trifluoromethyl 3-bromoallylic alcohols from 1,1-dibromo-1-alkenes.

Authors:  Youhua Li; Long Lu; Xiaoming Zhao
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005
View more
  17 in total

1.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

2.  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

3.  Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination.

Authors:  Brannon Sam; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-10       Impact factor: 15.336

4.  Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Synthesis (Stuttg)       Date:  2014-07-15       Impact factor: 3.157

Review 5.  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

6.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

7.  Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Org Lett       Date:  2015-04-24       Impact factor: 6.005

8.  Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors:  Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

9.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

10.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.