Literature DB >> 25030082

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines.

Edward J Cochrane1, Daniele Leonori, Lorraine A Hassall, Iain Coldham.   

Abstract

The chiral base n-BuLi/(-)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39-48% and ers up to 97 : 3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.

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Year:  2014        PMID: 25030082     DOI: 10.1039/c4cc04576a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  2 in total

1.  Kinetic Resolution of 2-Aryl-4-methylenepiperidines toward Enantioenriched Functionalizable Piperidine Fragments.

Authors:  Anthony Choi; Anthony J H M Meijer; Ilaria Proietti Silvestri; Iain Coldham
Journal:  J Org Chem       Date:  2022-06-14       Impact factor: 4.198

2.  Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench.

Authors:  Nicholas Carter; Xiabing Li; Lewis Reavey; Anthony J H M Meijer; Iain Coldham
Journal:  Chem Sci       Date:  2017-12-14       Impact factor: 9.825

  2 in total

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