Asymmetric isochalcogenourea-catalysed (4 + 2)-cycloadditions of <i>ortho</i>-quinone methides and allenoates

Chiral isochalcogenoureas (<i>i.e.</i> isothioureas and isoselenoureas) catalyse the asymmetric (4 + 2)-cycloaddition of various allenoates with <i>ortho</i>-quinone methides. This approach provides straightforward access to different chromane derivatives with high enantioselectivities, good yields, and control of the configuration of the exocyclic double bond. Furthermore, some of the novel <i>ortho</i>-quinone methides used herein were successfully integrated into the Mayr reactivity scale by determining their electrophilicity parameter.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-12-03
DOI
https://doi.org/10.1039/d4ob01855a
Citations
9
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
2.25

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article

Asymmetric isochalcogenourea-catalysed (4 + 2)-cycloadditions of ortho-quinone methides and allenoates

Armin R. Ofial, Magdalena Piringer, Anna Scheucher, Johanna Novacek et al.
9 citations
Organic & Biomolecular Chemistry
Synthesis of Indole Derivatives
2.25
article

Asymmetric isochalcogenourea-catalysed (4 + 2)-cycloadditions of ortho-quinone methides and allenoates

Armin R. Ofial, Magdalena Piringer, Anna Scheucher, Johanna Novacek, Mario Waser, Christoph Groß
article en
9 citations

Abstract

Chiral isochalcogenoureas (<i>i.e.</i> isothioureas and isoselenoureas) catalyse the asymmetric (4 + 2)-cycloaddition of various allenoates with <i>ortho</i>-quinone methides. This approach provides straightforward access to different chromane derivatives with high enantioselectivities, good yields, and control of the configuration of the exocyclic double bond. Furthermore, some of the novel <i>ortho</i>-quinone methides used herein were successfully integrated into the Mayr reactivity scale by determining their electrophilicity parameter.

Organic & Biomolecular ChemistryVol. 23(4)
Johannes Kepler University of Linz (AT), Ludwig-Maximilians-Universität München (DE)
Österreichische Nationalstiftung für Forschung, Technologie und Entwicklung, Austrian Science Fund
Openalex Percentile: Top 12%
Synthesis of Indole Derivatives
2.25
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