Literature DB >> 28603973

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

Michael Holmes1, Khoa D Nguyen1, Leyah A Schwartz1, Tom Luong1, Michael J Krische1.   

Abstract

Using an iridium catalyst modified by PhanePhos, CF3-allenes react with methanol to form branched products of hydrohydroxymethylation as single regioisomers with excellent levels of enantiomeric enrichment. This hydrogen autotransfer process enables catalytic enantioselective formation of acyclic CF3-bearing all-carbon quaternary stereocenters in the absence of stoichiometric metals or byproducts.

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Year:  2017        PMID： 28603973      PMCID： PMC5651675          DOI： 10.1021/jacs.7b04374

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


  62 in total

1.  Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates.

Authors:  Jing Nie; Hong-Chao Guo; Dominique Cahard; Jun-An Ma
Journal:  Chem Rev       Date:  2010-11-30       Impact factor: 60.622

Review 2.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

3.  Catalytic asymmetric fluorinations.

Authors:  Carla Bobbio; Véronique Gouverneur
Journal:  Org Biomol Chem       Date:  2006-05-03       Impact factor: 3.876

4.  Catalytic asymmetric fluorination comes of age.

Authors:  Vincent A Brunet; David O'Hagan
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2008-09       Impact factor: 60.622

Review 6.  Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?

Authors:  Dominique Cahard; Xiuhua Xu; Samuel Couve-Bonnaire; Xavier Pannecoucke
Journal:  Chem Soc Rev       Date:  2009-10-16       Impact factor: 54.564

7.  Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors:  Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

8.  Iridium-catalysed direct C-C coupling of methanol and allenes.

Authors:  Joseph Moran; Angelika Preetz; Ryan A Mesch; Michael J Krische
Journal:  Nat Chem       Date:  2011-02-27       Impact factor: 24.427

9.  Construction of optically active CF3-containing quaternary carbon centers via stereospecific S(N)2' reaction.

Authors:  Mitsuo Kimura; Takashi Yamazaki; Tomoya Kitazume; Toshio Kubota
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

10.  Enantioselective synthesis of trifluoromethyl-substituted cyclopropanes.

Authors:  Justin R Denton; Dinesh Sukumaran; Huw M L Davies
Journal:  Org Lett       Date:  2007-06-07       Impact factor: 6.005
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  25 in total

1.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

Review 2.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

3.  Catalytic One-Step Deoxytrifluoromethylation of Alcohols.

Authors:  Francisco de Azambuja; Sydney M Lovrien; Patrick Ross; Brett R Ambler; Ryan A Altman
Journal:  J Org Chem       Date:  2019-01-25       Impact factor: 4.354

4.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

5.  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

6.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

7.  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

8.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

9.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

10.  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
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