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

Jose I Martínez, Uxue Uria, Maria Muñiz, Efraím Reyes, Luisa Carrillo, Jose L Vicario

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Article in Beilstein journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

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2citing papers in PubMed

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3 · Its place in the literature

Who cites it

2 citing papers in PubMed.

DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.The Journal of organic chemistry · 2021
Article
H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020
Article

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5 · Who and what money

Authors and funding

6 authors.

Jose I MartínezDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Uxue UriaDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Maria MuñizDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Efraím ReyesDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Luisa CarrilloDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Jose L VicarioDepartment of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

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.

Indexed as

asymmetric diastereodivergentenantioselectiveMichael additionnitroalkenesnitroestersorganocatalysissquaramides

Identifiers

PMID26734103

DOI10.3762/bjoc.11.277

PMCPMC4685793

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