Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence

A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael–Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes be...

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Detalles Bibliográficos
Autores principales: Chauhan, Pankaj, Urbanietz, Gregor, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2014
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4268544/
https://www.ncbi.nlm.nih.gov/pubmed/24842728
http://dx.doi.org/10.1039/c4cc01885k
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author Chauhan, Pankaj
Urbanietz, Gregor
Raabe, Gerhard
Enders, Dieter
author_facet Chauhan, Pankaj
Urbanietz, Gregor
Raabe, Gerhard
Enders, Dieter
author_sort Chauhan, Pankaj
collection PubMed
description A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael–Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68–86%) and excellent stereoselectivities (>30 : 1 dr and 96–99% ee).
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spelling pubmed-42685442015-01-07 Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence Chauhan, Pankaj Urbanietz, Gregor Raabe, Gerhard Enders, Dieter Chem Commun (Camb) Chemistry A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael–Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68–86%) and excellent stereoselectivities (>30 : 1 dr and 96–99% ee). Royal Society of Chemistry 2014-07-04 2014-05-20 /pmc/articles/PMC4268544/ /pubmed/24842728 http://dx.doi.org/10.1039/c4cc01885k Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by-nc/2.0/uk/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Chauhan, Pankaj
Urbanietz, Gregor
Raabe, Gerhard
Enders, Dieter
Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title_full Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title_fullStr Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title_full_unstemmed Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title_short Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence
title_sort asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic michael–michael–1,2-addition sequence
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4268544/
https://www.ncbi.nlm.nih.gov/pubmed/24842728
http://dx.doi.org/10.1039/c4cc01885k
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