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

Matthew L. Clarke; Charlotte E. S. Jones; Marcia B. France

doi:10.1186/1860-5397-3-24

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

Matthew L. Clarke, Charlotte E. S. Jones, Marcia B. France

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Article number	24
Number of pages	4
Journal	Beilstein Journal of Organic Chemistry
Volume	3
DOIs	https://doi.org/10.1186/1860-5397-3-24
Publication status	Published - 14 Sept 2007

Keywords

ASYMMETRIC CATALYSIS
COMPLEXES
ACIDS

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10.1186/1860-5397-3-24

1860-5397-3-24
© 2007 Clarke et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://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: (http://www.beilstein-journals.org/bjoc)
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abstract = "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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doi = "10.1186/1860-5397-3-24",

language = "English",

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AU - France, Marcia B.

PY - 2007/9/14

Y1 - 2007/9/14

N2 - 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.

AB - 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.

KW - ASYMMETRIC CATALYSIS

KW - COMPLEXES

KW - ACIDS

UR - https://www.scopus.com/pages/publications/38149081322

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DO - 10.1186/1860-5397-3-24

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

Abstract

Keywords

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