Literature DB >> 22408286

CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

Timothy K Beng1, Robert E Gawley.   

Abstract

The diastereoselective synthesis of trans-2,6-disubstituted piperidines has been rendered enantioselective by incorporating a catalytic dynamic resolution into the first alkylation step. The method has been applied to the synthesis of (-)-epidihydropinidine and (+)-trans-lupetidine.

Entities:  

Year:  2012        PMID： 22408286      PMCID： PMC3295593          DOI： 10.3987/com-11-s(p)45

Source DB:  PubMed          Journal:  Heterocycles        ISSN： 0385-5414            Impact factor:   0.831


  15 in total

1.  No-D NMR (no-deuterium proton NMR) spectroscopy: a simple yet powerful method for analyzing reaction and reagent solutions.

Authors:  Thomas R Hoye; Brian M Eklov; Troy D Ryba; Mikhail Voloshin; Letitia J Yao
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

2.  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

3.  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

4.  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

5.  Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine.

Authors:  T J Wilkinson; N W Stehle; P Beak
Journal:  Org Lett       Date:  2000-01-27       Impact factor: 6.005

6.  Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines.

Authors:  Robert E Gawley; Daniel B Eddings; Marcelina Santiago; Davic A Vicic
Journal:  Org Biomol Chem       Date:  2006-10-20       Impact factor: 3.876

7.  Highly diastereoselective arylations of substituted piperidines.

Authors:  Stephanie Seel; Tobias Thaler; Keishi Takatsu; Cong Zhang; Hendrik Zipse; Bernd F Straub; Peter Mayer; Paul Knochel
Journal:  J Am Chem Soc       Date:  2011-03-09       Impact factor: 15.419

8.  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

9.  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

10.  Syntheses of (+)- and (-)-dihydropinidine and (+)- and (-)-epidihydropinidine by using yeast reduction of methyl (2-oxocyclohexyl)acetate.

Authors:  Satoshi Yamauchi; Shunji Mori; Yoshio Hirai; Yoshiro Kinoshita
Journal:  Biosci Biotechnol Biochem       Date:  2004-03       Impact factor: 2.043
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  1 in total

1.  Dynamics of catalytic resolution of 2-lithio-N-Boc-piperidine by ligand exchange.

Authors:  Timothy K Beng; William S Tyree; Trent Parker; Chicheung Su; Paul G Williard; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2012-09-25       Impact factor: 15.419
  1 in total

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