Literature DB >> 19159275

Rapid, general access to chiral beta-fluoroamines and beta,beta-difluoroamines via organocatalysis.

Olugbeminiyi O Fadeyi1, Craig W Lindsley.   

Abstract

A rapid, general route to enantiopure beta-fluoroamines and beta,beta-difluoroamines has been developed employing organocatalysis in both a two-pot and a one-pot procedure. Both chemical yields (64-82%) and enantioselectivity (94-98% ee) were excellent and represent a significant improvement in the art of preparing chemically diverse beta-fluoroamines from readily available precursors.

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Year:  2009        PMID： 19159275      PMCID： PMC3192010          DOI： 10.1021/ol802930q

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


  5 in total

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Journal:  J Med Chem       Date:  2008-06-21       Impact factor: 7.446

2.  Enantioselective organocatalytic alpha-fluorination of aldehydes.

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Review 3.  Fluorine in medicinal chemistry.

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Review 4.  Predicting and tuning physicochemical properties in lead optimization: amine basicities.

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Journal:  ChemMedChem       Date:  2007-08       Impact factor: 3.466

5.  Design and synthesis of 2- and 3-substituted-3-phenylpropyl analogs of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine: role of amino, fluoro, hydroxyl, methoxyl, methyl, methylene, and oxo substituents on affinity for the dopamine and serotonin transporters.

Authors:  Ling-Wei Hsin; Li-Te Chang; Richard B Rothman; Christina M Dersch; Arthur E Jacobson; Kenner C Rice
Journal:  J Med Chem       Date:  2008-04-05       Impact factor: 7.446
  5 in total
  17 in total

1.  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

2.  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

3.  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

4.  Organocatalytic enantioselective olefin aminofluorination.

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Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

5.  A novel class of H3 antagonists derived from the natural product guided synthesis of unnatural analogs of the marine bromopyrrole alkaloid dispyrin.

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6.  An asymmetric total synthesis of brevisamide.

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7.  Further exploration of M₁ allosteric agonists: subtle structural changes abolish M₁ allosteric agonism and result in pan-mAChR orthosteric antagonism.

Authors:  Douglas J Sheffler; Christian Sevel; Uyen Le; Kimberly M Lovell; James C Tarr; Sheridan J S Carrington; Hyekyung P Cho; Gregory J Digby; Colleen M Niswender; P Jeffrey Conn; Corey R Hopkins; Michael R Wood; Craig W Lindsley
Journal:  Bioorg Med Chem Lett       Date:  2012-11-09       Impact factor: 2.823

8.  Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N'-protected piperazines via organocatalysis.

Authors:  Matthew C O'Reilly; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2011-12-29       Impact factor: 2.415

9.  A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

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Journal:  Proc Natl Acad Sci U S A       Date:  2013-08-06       Impact factor: 11.205

10.  Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.

Authors:  Katrina M Mennie; Steven M Banik; Elaine C Reichert; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2018-03-29       Impact factor: 15.419
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