Literature DB >> 17629284

Copper(I) alkoxide-catalyzed alkynylation of trifluoromethyl ketones.

Rie Motoki1, Motomu Kanai, Masakatsu Shibasaki.   

Abstract

A general method for direct alkynylation of trifluoromethyl ketones was developed by using CuO(t)Bu-xantphos or phenanthroline complexes as catalysts. The ligands significantly enhanced the catalyst activity. In addition, KOTf, generated in the catalyst preparation step, exhibited some acceleration effects. A preliminary extension to a catalytic enantioselective CF3-substituted tertiary propargyl alcohol synthesis (up to 52% ee) is also described.

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Year:  2007        PMID： 17629284     DOI： 10.1021/ol071003k

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


  9 in total

1.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

2.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

3.  Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.

Authors:  Farid W van der Mei; Changming Qin; Ryan J Morrison; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2017-06-24       Impact factor: 15.419

4.  Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones.

Authors:  Nicholas W Mszar; Malte S Mikus; Sebastian Torker; Fredrik Haeffner; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-21       Impact factor: 15.336

5.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

Review 6.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

Review 7.  Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions.

Authors:  Jixin Liu; Srimoyee Dasgupta; Mary P Watson
Journal:  Beilstein J Org Chem       Date:  2015-12-22       Impact factor: 2.883

8.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

Authors:  Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

9.  Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH···O/sp3-CH···O two-point hydrogen bonding combined with dispersive attractions.

Authors:  Martin C Schwarzer; Akane Fujioka; Takaoki Ishii; Hirohisa Ohmiya; Seiji Mori; Masaya Sawamura
Journal:  Chem Sci       Date:  2018-02-28       Impact factor: 9.825
  9 in total

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