Literature DB >> 28560721

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

Nicholas W Mszar1, Malte S Mikus1, Sebastian Torker1, Fredrik Haeffner1, Amir H Hoveyda1.   

Abstract

A broadly applicable, practical, scalable, efficient and highly α- and enantioselective method for addition of a silyl-protected propargyl moiety to trifluoromethyl ketones has been developed. Reactions, promoted by 2.0 mol % of a catalyst that is derived in situ from a readily accessible aminophenol compound at ambient temperature, were complete after only 15 minutes at room temperature. The desired tertiary alcohols were isolated in up to 97 % yield and 98.5:1.5 enantiomeric ratio. Alkyl-, alkenyl-, alkynyl-, aryl- or heteroaryl-substituted trifluoromethyl ketones can be used. Utility is highlighted by application to a transformation that is relevant to enantioselective synthesis of BI 653048, a compound active against rheumatoid arthritis.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  catalysis; enantioselective synthesis; homopropargylic alcohols; propargyl groups; trifluoromethyl group

Mesh：

Substances：

Year:  2017        PMID： 28560721      PMCID： PMC5535737          DOI： 10.1002/anie.201703844

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  24 in total

1.  Non-steroidal dissociated glucocorticoid agonists: indoles as A-ring mimetics and function-regulating pharmacophores.

Authors:  Raj Betageri; Thomas Gilmore; Daniel Kuzmich; Thomas M Kirrane; Jörg Bentzien; Dieter Wiedenmayer; Younes Bekkali; John Regan; Angela Berry; Bachir Latli; Alison J Kukulka; Tazmeen N Fadra; Richard M Nelson; Susan Goldrick; Ljiljana Zuvela-Jelaska; Don Souza; Josephine Pelletier; Roger Dinallo; Mark Panzenbeck; Carol Torcellini; Heewon Lee; Edward Pack; Christian Harcken; Gerald Nabozny; David S Thomson
Journal:  Bioorg Med Chem Lett       Date:  2011-09-10       Impact factor: 2.823

2.  Trifluoromethyl group as a pharmacophore: effect of replacing a CF3 group on binding and agonist activity of a glucocorticoid receptor ligand.

Authors:  Raj Betageri; Yan Zhang; Renee M Zindell; Daniel Kuzmich; Thomas M Kirrane; Jörg Bentzien; Mario Cardozo; Alison J Capolino; Tazmeen N Fadra; Richard M Nelson; Zofia Paw; Daw-Tsun Shih; Cheng-Kon Shih; Ljiljana Zuvela-Jelaska; Gerald Nabozny; David S Thomson
Journal:  Bioorg Med Chem Lett       Date:  2005-11-01       Impact factor: 2.823

3.  Assessing the bioisosterism of the trifluoromethyl group with a protease probe.

Authors:  Monika Jagodzinska; Florent Huguenot; Gabriele Candiani; Matteo Zanda
Journal:  ChemMedChem       Date:  2009-01       Impact factor: 3.466

4.  Organic fluorine compounds: a great opportunity for enhanced materials properties.

Authors:  Ricarda Berger; Giuseppe Resnati; Pierangelo Metrangolo; Edwin Weber; Jürg Hulliger
Journal:  Chem Soc Rev       Date:  2011-03-30       Impact factor: 54.564

5.  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

6.  Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors:  Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-09       Impact factor: 15.336

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

Authors:  Rie Motoki; Motomu Kanai; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2007-07-13       Impact factor: 6.005

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.  An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst.

Authors:  Hao Wu; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

10.  Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.

Authors:  KyungA Lee; Daniel L Silverio; Sebastian Torker; Daniel W Robbins; Fredrik Haeffner; Farid W van der Mei; Amir H Hoveyda
Journal:  Nat Chem       Date:  2016-05-23       Impact factor: 24.427
View more
  4 in total

1.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

2.  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

3.  Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NH2 -Amines by Reactions Facilitated by a Threonine-Based Boron-Containing Catalyst.

Authors:  Diana C Fager; Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

4.  γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.

Authors:  Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-01       Impact factor: 15.336
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.