Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality

The asymmetric and catalytic Michael reaction between α-nitroesters and nitroalkenes has been studied in the presence of two bifunctional catalysts both containing the same absolute chirality at the carbon backbone. The reaction performed in similar conditions allows us to control the syn or anti se...

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Main Authors:	Jose I. Martínez, Uxue Uria, Maria Muñiz, Efraím Reyes, Luisa Carrillo, Jose L. Vicario
Format:	Article
Language:	English
Published:	Beilstein-Institut 2015-12-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	asymmetric diastereodivergent enantioselective Michael addition nitroalkenes nitroesters organocatalysis squaramides
Online Access:	https://doi.org/10.3762/bjoc.11.277

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spelling	doaj-fd9be3fbe978495d93839551d964679f2021-02-02T00:12:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-12-011112577258310.3762/bjoc.11.2771860-5397-11-277Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chiralityJose I. Martínez0Uxue Uria1Maria Muñiz2Efraím Reyes3Luisa Carrillo4Jose L. Vicario5Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainThe asymmetric and catalytic Michael reaction between α-nitroesters and nitroalkenes has been studied in the presence of two bifunctional catalysts both containing the same absolute chirality at the carbon backbone. The reaction performed in similar conditions allows us to control the syn or anti selectivity of the Michael adduct obtaining good yields and high enantiocontrol in all cases.https://doi.org/10.3762/bjoc.11.277asymmetric diastereodivergentenantioselectiveMichael additionnitroalkenesnitroestersorganocatalysissquaramides
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Jose I. Martínez Uxue Uria Maria Muñiz Efraím Reyes Luisa Carrillo Jose L. Vicario
spellingShingle	Jose I. Martínez Uxue Uria Maria Muñiz Efraím Reyes Luisa Carrillo Jose L. Vicario Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality Beilstein Journal of Organic Chemistry asymmetric diastereodivergent enantioselective Michael addition nitroalkenes nitroesters organocatalysis squaramides
author_facet	Jose I. Martínez Uxue Uria Maria Muñiz Efraím Reyes Luisa Carrillo Jose L. Vicario
author_sort	Jose I. Martínez
title	Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality
title_short	Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality
title_full	Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality
title_fullStr	Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality
title_full_unstemmed	Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality
title_sort	organocatalytic and enantioselective michael reaction between α-nitroesters and nitroalkenes. syn/anti-selectivity control using catalysts with the same absolute backbone chirality
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2015-12-01
description	The asymmetric and catalytic Michael reaction between α-nitroesters and nitroalkenes has been studied in the presence of two bifunctional catalysts both containing the same absolute chirality at the carbon backbone. The reaction performed in similar conditions allows us to control the syn or anti selectivity of the Michael adduct obtaining good yields and high enantiocontrol in all cases.
topic	asymmetric diastereodivergent enantioselective Michael addition nitroalkenes nitroesters organocatalysis squaramides
url	https://doi.org/10.3762/bjoc.11.277
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Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality

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