Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence

The asymmetric organocatalytic one-pot synthesis of trans-3,4-disubstituted 3,4-dihydroisoquinolin-1(2H)-ones is described. Starting from 2-(nitromethyl)benzaldehydes and various N-protected aldimines, 5 mol% of a quinine-based squaramide organocatalyst was used to synthesize the title compounds as...

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Detalles Bibliográficos
Autores principales: Hahn, Robert, Jafari, Ehsan, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4693956/
https://www.ncbi.nlm.nih.gov/pubmed/26722132
http://dx.doi.org/10.1055/s-0034-1379398
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author Hahn, Robert
Jafari, Ehsan
Raabe, Gerhard
Enders, Dieter
author_facet Hahn, Robert
Jafari, Ehsan
Raabe, Gerhard
Enders, Dieter
author_sort Hahn, Robert
collection PubMed
description The asymmetric organocatalytic one-pot synthesis of trans-3,4-disubstituted 3,4-dihydroisoquinolin-1(2H)-ones is described. Starting from 2-(nitromethyl)benzaldehydes and various N-protected aldimines, 5 mol% of a quinine-based squaramide organocatalyst was used to synthesize the title compounds as virtually single diastereomers via an aza-Henry–hemiaminalization–oxidation sequence. Moderate to good yields (39–78%) and moderate to very good enantioselectivities (40–95% ee) were reached.
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spelling pubmed-46939562015-12-29 Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence Hahn, Robert Jafari, Ehsan Raabe, Gerhard Enders, Dieter Synthesis (Stuttg) Article The asymmetric organocatalytic one-pot synthesis of trans-3,4-disubstituted 3,4-dihydroisoquinolin-1(2H)-ones is described. Starting from 2-(nitromethyl)benzaldehydes and various N-protected aldimines, 5 mol% of a quinine-based squaramide organocatalyst was used to synthesize the title compounds as virtually single diastereomers via an aza-Henry–hemiaminalization–oxidation sequence. Moderate to good yields (39–78%) and moderate to very good enantioselectivities (40–95% ee) were reached. 2015-02-01 /pmc/articles/PMC4693956/ /pubmed/26722132 http://dx.doi.org/10.1055/s-0034-1379398 Text en License terms: CC BY-NC-ND (http://creativecommons.org/licenses/by-nc-nd/4.0/)
spellingShingle Article
Hahn, Robert
Jafari, Ehsan
Raabe, Gerhard
Enders, Dieter
Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title_full Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title_fullStr Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title_full_unstemmed Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title_short Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence
title_sort organocatalytic asymmetric synthesis of dihydroisoquinolinones via a one-pot aza-henry–hemiaminalization–oxidation sequence
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4693956/
https://www.ncbi.nlm.nih.gov/pubmed/26722132
http://dx.doi.org/10.1055/s-0034-1379398
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