Literature DB >> 26270567

Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines.

James C Anderson1, Joshua P Barham1, Christopher D Rundell1.   

Abstract

Reductive cyclization of 2-iminonitrostyrenes (from the condensation of 2-aminostyrenes with an aldehyde and subsequent nitration of the alkene) using a bifunctional thiourea catalyst and tert-butyl-Hantzsch ester leads to an intramolecular conjugate hydride addition nitro-Mannich reaction to give the corresponding cis-2-aryl-3-nitrotetrahydroquinolines as single diastereoisomers in high yields and enantioselectivities.

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Year:  2015        PMID: 26270567     DOI: 10.1021/acs.orglett.5b02036

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


  2 in total

1.  β-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.

Authors:  Ahmad S Altiti; Kai Fan Cheng; Mingzhu He; Yousef Al-Abed
Journal:  Chemistry       Date:  2017-07-26       Impact factor: 5.236

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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