ArticleOrganic & biomolecular chemistry2016
Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies.
Article in Organic & biomolecular chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Unveiling the dual-state emissive behaviour of 4,6-diarylpyrimidin-2-amines through a plug-and-play approach.Scientific reports · 2024Article
- Catalytic, Enantioselective Cycloaddition of Pyrrole-2Organic letters · 2024Article
- Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-Additions.ChemistryEurope · 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
- An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis.Organic & biomolecular chemistry · 2019Article
- Crystal structure and synthesis of 3-(1Acta crystallographica. Section E, Crystallographic communications · 2018Article
- 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis.Chemical communications (Cambridge, England) · 2017Article
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
The catalytic enantioselective synthesis of a range of cis-pyrrolizine carboxylate derivatives with outstanding stereocontrol (14 examples, >95 : 5 dr, >98 : 2 er) through an isothiourea-catalyzed intramolecular Michael addition-lactonisation and ring-opening approach from the corresponding enone acid is reported. An optimised and straightforward three-step synthetic route to the enone acid starting materials from readily available pyrrole-2-carboxaldehydes is delineated, with benzotetramisole (5 mol%) proving the optimal catalyst for the enantioselective process. Ring-opening of the pyrrolizine dihydropyranone products with either MeOH or a range of amines leads to the desired products in excellent yield and enantioselectivity. Computation has been used to probe the factors leading to high stereocontrol, with the formation of the observed cis-steroisomer predicted to be kinetically and thermodynamically favoured.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.