Literature DB >> 22881214

Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines.

Timothy K Beng1, Jin Sun Woo, Robert E Gawley.   

Abstract

In diethyl ether, N-Boc-2-lithio-2-arylpiperidines have been found to be configurationally stable at -80 °C, whereas N-Boc-2-lithio-2-arylpyrrolidines are configurationally stable at -60 °C. Several tertiary benzylic carbanions derived from enantioenriched 2-aryl heterocycles have been successfully alkylated or acylated with little to no loss of enantiopurity. The scope of the reactions has been explored. The enantiomerization dynamics of N-Boc-2-lithio-2-phenylpyrrolidine and N-Boc-2-lithio-2-phenylpiperidine have been studied in the presence of different solvents and achiral ligands.

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Year:  2012        PMID： 22881214      PMCID： PMC3443602          DOI： 10.1021/ja306276w

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


  21 in total

1.  Remarkable amplification of the self-disproportionation of enantiomers on achiral-phase chromatography columns.

Authors:  Vadim A Soloshonok
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-23       Impact factor: 15.336

2.  Dynamic thermodynamic resolution: advantage by separation of equilibration and resolution.

Authors:  Won Koo Lee; Yong Sun Park; Peter Beak
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

3.  Dynamic resolution of N-Boc-2-lithiopiperidine.

Authors:  Iain Coldham; Sophie Raimbault; Praful T Chovatia; Jignesh J Patel; Daniele Leonori; Nadeem S Sheikh; David T E Whittaker
Journal:  Chem Commun (Camb)       Date:  2008-08-08       Impact factor: 6.222

4.  Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds.

Authors:  Robert E Gawley
Journal:  Top Stereochem       Date:  2010-01-01

5.  Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines.

Authors:  Timothy K Beng; Robert E Gawley
Journal:  Org Lett       Date:  2010-12-21       Impact factor: 6.005

6.  Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Authors:  Graeme Barker; Julia L McGrath; Artis Klapars; Darren Stead; George Zhou; Kevin R Campos; Peter O'Brien
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

7.  Asymmetric deprotonation of N-boc piperidine: react IR monitoring and mechanistic aspects.

Authors:  Darren Stead; Giorgio Carbone; Peter O'Brien; Kevin R Campos; Iain Coldham; Adam Sanderson
Journal:  J Am Chem Soc       Date:  2010-06-02       Impact factor: 15.419

8.  A theoretical investigation into the inversion barrier of dipole-stabilized alpha-aminoorganolithiums.

Authors:  Fredrik Haeffner; Peter Brandt; Robert E Gawley
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

9.  Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: synthesis of (R)-(+)-N-Boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-beta-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C.

Authors:  Timothy K Beng; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

10.  Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors:  Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419
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  4 in total

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Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates.

Authors:  Timothy K Beng; Hironori Takeuchi; Manuel Weber; Richmond Sarpong
Journal:  Chem Commun (Camb)       Date:  2015-05-04       Impact factor: 6.222

3.  Direct α-C-H bond functionalization of unprotected cyclic amines.

Authors:  Weijie Chen; Longle Ma; Anirudra Paul; Daniel Seidel
Journal:  Nat Chem       Date:  2017-11-06       Impact factor: 24.427

Review 4.  Application of Biobased Solvents in Asymmetric Catalysis.

Authors:  Margherita Miele; Veronica Pillari; Vittorio Pace; Andrés R Alcántara; Gonzalo de Gonzalo
Journal:  Molecules       Date:  2022-10-08       Impact factor: 4.927
  4 in total

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