Parallel Kinetic Resolution of Intramolecular Furan Diels‐Alder Cycloadducts via Asymmetric Hydroboration

Parallel Kinetic Resolution of Intramolecular Furan Diels‐Alder Cycloadducts via Asymmetric Hydroboration

We report parallel kinetic resolution of intramolecular Diels‐Alder cycloadducts, where up to five stereocentres are defined using asymmetric hydroboration as the enantiodiscriminating reaction, and reveal evidence for dynamic kinetic resolution based on a reversible cycloaddition. Simple, parallel...

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Veröffentlicht in:European journal of organic chemistry 2019-11, Vol.2019 (43), p.7223-7227
Hauptverfasser: Fulgheri, Tamara, Cornwall, Philip, Turner, Andrew R., Sweeney, Joseph B., Gill, Duncan M.
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetry
Cycloaddition
Enantioselectivity
Hydroboration
Kinetic resolution
Regioselectivity
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Zusammenfassung:We report parallel kinetic resolution of intramolecular Diels‐Alder cycloadducts, where up to five stereocentres are defined using asymmetric hydroboration as the enantiodiscriminating reaction, and reveal evidence for dynamic kinetic resolution based on a reversible cycloaddition. Simple, parallel and dynamic: asymmetric hydroboration reactions of racemic intramolecular Diels‐Alder furan (IMDAF) cycloadducts give regiodivergent outcomes in which simple, parallel and dynamic kinetic resolutions of the substrate enantiomers may be observed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901407