The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas

Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enan...

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Detalles Bibliográficos
Autores principales: Clarke, Matthew L, Jones, Charlotte E S, France, Marcia B
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2007
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2176055/
https://www.ncbi.nlm.nih.gov/pubmed/17868454
http://dx.doi.org/10.1186/1860-5397-3-24
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author Clarke, Matthew L
Jones, Charlotte E S
France, Marcia B
author_facet Clarke, Matthew L
Jones, Charlotte E S
France, Marcia B
author_sort Clarke, Matthew L
collection PubMed
description Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enantioselectivity (up to 33% e.e.) and low turnover frequencies.
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spelling pubmed-21760552008-01-09 The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas Clarke, Matthew L Jones, Charlotte E S France, Marcia B Beilstein J Org Chem Preliminary Communication Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enantioselectivity (up to 33% e.e.) and low turnover frequencies. Beilstein-Institut 2007-09-14 /pmc/articles/PMC2176055/ /pubmed/17868454 http://dx.doi.org/10.1186/1860-5397-3-24 Text en Copyright © 2007, Clarke et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Clarke, Matthew L
Jones, Charlotte E S
France, Marcia B
The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title_full The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title_fullStr The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title_full_unstemmed The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title_short The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
title_sort first organocatalytic carbonyl-ene reaction: isomerisation-free c-c bond formations catalysed by h-bonding thio-ureas
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2176055/
https://www.ncbi.nlm.nih.gov/pubmed/17868454
http://dx.doi.org/10.1186/1860-5397-3-24
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