Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of t...

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Main Authors:	Sergei Žari, Tiiu Kailas, Marina Kudrjashova, Mario Öeren, Ivar Järving, Toomas Tamm, Margus Lopp, Tõnis Kanger
Format:	Article
Language:	English
Published:	Beilstein-Institut 2012-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	Michael addition non-covalent catalysis organocatalysis squaramide thiourea
Online Access:	https://doi.org/10.3762/bjoc.8.165

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spelling	doaj-d9dce444c75c47af81065aa7936c60582021-02-02T04:44:50ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-09-01811452145710.3762/bjoc.8.1651860-5397-8-165Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketonesSergei Žari0Tiiu Kailas1Marina Kudrjashova2Mario Öeren3Ivar Järving4Toomas Tamm5Margus Lopp6Tõnis Kanger7Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaDepartment of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, EstoniaThe organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a.https://doi.org/10.3762/bjoc.8.165Michael additionnon-covalent catalysisorganocatalysissquaramidethiourea
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Sergei Žari Tiiu Kailas Marina Kudrjashova Mario Öeren Ivar Järving Toomas Tamm Margus Lopp Tõnis Kanger
spellingShingle	Sergei Žari Tiiu Kailas Marina Kudrjashova Mario Öeren Ivar Järving Toomas Tamm Margus Lopp Tõnis Kanger Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones Beilstein Journal of Organic Chemistry Michael addition non-covalent catalysis organocatalysis squaramide thiourea
author_facet	Sergei Žari Tiiu Kailas Marina Kudrjashova Mario Öeren Ivar Järving Toomas Tamm Margus Lopp Tõnis Kanger
author_sort	Sergei Žari
title	Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_short	Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_full	Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_fullStr	Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_full_unstemmed	Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
title_sort	organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2012-09-01
description	The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a.
topic	Michael addition non-covalent catalysis organocatalysis squaramide thiourea
url	https://doi.org/10.3762/bjoc.8.165
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Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

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