Catalytic Enantioselective Intramolecular Aza-Michael Addition to α,β-Unsaturated Esters.

Evan G W Rutter, Cameron J MacRae, Haoran Xiong, Daniel Rozsar, Katherine F P Clarke, Darren J Dixon

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

What it found

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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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0 citing papers in PubMed.

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4 · The record

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5 · Who and what money

Authors and funding

6 authors.

Evan G W RutterDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.ORCID https://orcid.org/0009-0007-7073-6725

Cameron J MacRaeDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.ORCID https://orcid.org/0009-0009-2552-5755

Haoran XiongDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.

Daniel RozsarDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.ORCID https://orcid.org/0000-0002-0516-1722

Katherine F P ClarkeDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.ORCID https://orcid.org/0009-0003-8952-1872

Darren J DixonDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.ORCID https://orcid.org/0000-0003-2456-5236

Funding

EPSRC Centre for Doctoral Training in Inorganic Chemistry for Future Manufacturing EP/S023828/1EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine EP/L015838/1

6 · The paper itself

Abstract

A bifunctional iminophosphorane (BIMP)-catalyzed enantioselective intramolecular aza-Michael reaction of sulfonamides to tethered α,β-unsaturated esters is described. Reactivity toward traditionally challenging ester Michael acceptors is achieved through careful catalyst design, enabling the synthesis of enantioenriched pyrrolidines, piperidines, and indoline derivatives in excellent yields (up to 99%) and enantiomeric ratios (up to 97.5:2.5 er) under operationally simple conditions. The broad reaction scope demonstrates excellent tolerance to variation in the sulfonamide group, the Michael acceptor, and substituents on the tether in between. Furthermore, the synthetic utility of the method is highlighted by gram-scale reactions at reduced catalyst loadings and by downstream derivatization of multiple enantiopure products.

Indexed as

enantioselective catalysisenantioselectivityMichael additionnitrogen heterocyclesorganocatalysis

Identifiers

PMID42251643

DOI10.1002/anie.5995443

PMCPMC13383253

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LicenceCC BY

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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 Socratic graph.