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Stereoselective Synthesis of Densely Substituted Tetrahydroquinolines by a Conjugate Addition Nitro-Mannich Reaction with Carbon Nucleophiles

Anderson, JC; Rundell, CD; (2016) Stereoselective Synthesis of Densely Substituted Tetrahydroquinolines by a Conjugate Addition Nitro-Mannich Reaction with Carbon Nucleophiles. Synlett , 27 (1) pp. 41-44. 10.1055/s-0035-1560815. Green open access

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Abstract

Conjugate addition of an alkyl group to a series of 2-imino-nitrostyrenes and then addition of trifluoroacetic acid initiates a nitro-Mannich cyclisation to give cis,cis-2,3,4-substituted tetrahydroquinolines in good yield and high diastereoselectivity.

Type: Article
Title: Stereoselective Synthesis of Densely Substituted Tetrahydroquinolines by a Conjugate Addition Nitro-Mannich Reaction with Carbon Nucleophiles
Open access status: An open access version is available from UCL Discovery
DOI: 10.1055/s-0035-1560815
Publisher version: http://dx.doi.org/10.1055/s-0035-1560815
Language: English
Additional information: © Georg Thieme Verlag Stuttgart · New York
Keywords: amines, stereoselective synthesis, cyclisation, imines, quinolines
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1472076
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