ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- DiastereodivergentChemical science · 2023Article
- Catalytic enantioselective synthesis of 1,4-dihydropyridinesChemical science · 2021Article
- Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives.Chemical science · 2020Article
- Quantum Reality in the Selective Reduction of a Benzofuran System.Molecules (Basel, Switzerland) · 2019Article
- Enantioselective synthesis of cyclopenta[Chemical science · 2017Article
- 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis.Chemical communications (Cambridge, England) · 2017Article
- Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies.Organic & biomolecular chemistry · 2016Article
- Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis.Chemistry, an Asian journal · 2016Article
- Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r.syn/anti , 99 % eesyn ), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r.syn/anti , 99 % eeanti ).
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