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

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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Main Authors: Matthew L. Clarke, Charlotte E. S. Jones, Marcia B. France
Format: Article
Language:English
Published: Beilstein-Institut 2007-09-01
Series:Beilstein Journal of Organic Chemistry
Online Access:https://doi.org/10.1186/1860-5397-3-24
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spelling doaj-148b177a58664acfa72dcee9a92547062021-02-02T06:47:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972007-09-01312410.1186/1860-5397-3-241860-5397-3-24The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureasMatthew L. Clarke0Charlotte E. S. Jones1Marcia B. France2School of Chemistry, University of St. Andrews, EaStCHEM, St. Andrews, Fife, KY16 9ST, UKSchool of Chemistry, University of St. Andrews, EaStCHEM, St. Andrews, Fife, KY16 9ST, UKDepartment of Chemistry, Washington and Lee University, Lexington, VA 24450, USAIntramolecular 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.https://doi.org/10.1186/1860-5397-3-24
collection DOAJ
language English
format Article
sources DOAJ
author Matthew L. Clarke
Charlotte E. S. Jones
Marcia B. France
spellingShingle Matthew L. Clarke
Charlotte E. S. Jones
Marcia B. France
The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas
Beilstein Journal of Organic Chemistry
author_facet Matthew L. Clarke
Charlotte E. S. Jones
Marcia B. France
author_sort Matthew L. Clarke
title 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_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_sort first organocatalytic carbonyl-ene reaction: isomerisation-free c-c bond formations catalysed by h-bonding thio-ureas
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2007-09-01
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.
url https://doi.org/10.1186/1860-5397-3-24
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