Literature DB >> 24039308

A general, enantioselective synthesis of β- and γ-fluoroamines.

Matthew C O'Reilly1, Craig W Lindsley.   

Abstract

In this Letter, we describe a short, high yielding protocol for the enantioselective (87-96% ee) and general synthesis of β-fluoroamines and previously difficult to access γ-fluoroamines from commercial aldehydes via organocatalysis.

Entities:  

Keywords:  Enantioselective; Organocatalysis; β-fluoroamine; γ-fluoroamine

Year:  2013        PMID： 24039308      PMCID： PMC3769685          DOI： 10.1016/j.tetlet.2013.04.116

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

1.  Reaction of InCl3 with various reducing agents: InCl3-NaBH4-mediated reduction of aromatic and aliphatic nitriles to primary amines.

Authors:  Jaime Z Saavedra; Angel Resendez; Alexander Rovira; Scott Eagon; Dustin Haddenham; Bakthan Singaram
Journal:  J Org Chem       Date:  2011-12-22       Impact factor: 4.354

2.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

3.  Highly enantioselective direct organocatalytic alpha-chlorination of ketones.

Authors:  Mauro Marigo; Stephan Bachmann; Nis Halland; Alan Braunton; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-18       Impact factor: 15.336

4.  A general, enantioselective synthesis of protected morpholines and piperazines.

Authors:  Matthew C O'Reilly; Craig W Lindsley
Journal:  Org Lett       Date:  2012-05-22       Impact factor: 6.005

5.  Enantioselective organocatalytic alpha-fluorination of aldehydes.

Authors:  Teresa D Beeson; David W C Macmillan
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  Highly efficient diastereoselective reduction of alpha-fluoroimines.

Authors:  Roy M Malamakal; Whitney R Hess; Todd A Davis
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

7.  Direct organocatalytic asymmetric alpha-chlorination of aldehydes.

Authors:  Nis Halland; Alan Braunton; Stephan Bachmann; Mauro Marigo; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

8.  Discovery of 1,4-substituted piperidines as potent and selective inhibitors of T-type calcium channels.

Authors:  Zhi-Qiang Yang; James C Barrow; William D Shipe; Kelly-Ann S Schlegel; Youheng Shu; F Vivien Yang; Craig W Lindsley; Kenneth E Rittle; Mark G Bock; George D Hartman; Victor N Uebele; Cindy E Nuss; Steve V Fox; Richard L Kraus; Scott M Doran; Thomas M Connolly; Cuyue Tang; Jeanine E Ballard; Yuhsin Kuo; Emily D Adarayan; Thomayant Prueksaritanont; Matthew M Zrada; Michael J Marino; Valerie Kuzmick Graufelds; Anthony G DiLella; Ian J Reynolds; Hugo M Vargas; Patricia B Bunting; Richard F Woltmann; Michael M Magee; Kenneth S Koblan; John J Renger
Journal:  J Med Chem       Date:  2008-09-26       Impact factor: 7.446

9.  Design, synthesis, and evaluation of a novel 4-aminomethyl-4-fluoropiperidine as a T-type Ca2+ channel antagonist.

Authors:  William D Shipe; James C Barrow; Zhi-Qiang Yang; Craig W Lindsley; F Vivien Yang; Kelly-Ann S Schlegel; Youheng Shu; Kenneth E Rittle; Mark G Bock; George D Hartman; Cuyue Tang; Jeanine E Ballard; Yuhsin Kuo; Emily D Adarayan; Thomayant Prueksaritanont; Matthew M Zrada; Victor N Uebele; Cindy E Nuss; Thomas M Connolly; Scott M Doran; Steven V Fox; Richard L Kraus; Michael J Marino; Valerie Kuzmick Graufelds; Hugo M Vargas; Patricia B Bunting; Martha Hasbun-Manning; Rose M Evans; Kenneth S Koblan; John J Renger
Journal:  J Med Chem       Date:  2008-06-10       Impact factor: 7.446

Review 10.  Understanding organofluorine chemistry. An introduction to the C-F bond.

Authors:  David O'Hagan
Journal:  Chem Soc Rev       Date:  2007-10-17       Impact factor: 54.564
View more
  3 in total

1.  Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.

Authors:  Brandon A Vara; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

2.  Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.

Authors:  Ying He; Zhenyu Yang; Richard T Thornbury; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

3.  Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines.

Authors:  Giulia Roagna; David M H Ascough; Francesco Ibba; Anna Chiara Vicini; Alberto Fontana; Kirsten E Christensen; Aldo Peschiulli; Daniel Oehlrich; Antonio Misale; Andrés A Trabanco; Robert S Paton; Gabriele Pupo; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-08-05       Impact factor: 15.419
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.