Iridium-catalyzed asymmetric cascade allylation/lactonization of methyl salicylates: enantioselective construction of chiral benzodioxepinones

An efficient asymmetric cascade allylation/lactonization of methyl salicylates has been achieved. The utilization of chiral-bridged biphenyl phosphoramidite ligand L3 resulted in good yields (up to 85%) and enantioselectivity (up to 95% ee) for the construction of a wide range of chiral benzodioxepi...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2025-01, Vol.12 (1), p.217-223
Main Authors: Pan, Bendu, Wu, Yunru, Zhang, Yaqi, He, Xiaobo, Long, Jiang, Qiu, Liqin
Format: Article
Language:English
Subjects:
Allyl compounds
Asymmetry
Chemical reactions
Enantiomers
Iridium
Ligands
Salicylates
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Summary:An efficient asymmetric cascade allylation/lactonization of methyl salicylates has been achieved. The utilization of chiral-bridged biphenyl phosphoramidite ligand L3 resulted in good yields (up to 85%) and enantioselectivity (up to 95% ee) for the construction of a wide range of chiral benzodioxepinones with tolerance to diverse substituents. This reaction is featured by low catalyst loading, commercially available substrates and a broad substrate scope. Control experiments indicate that a relay catalytic pathway and kinetic resolution of racemic VEC might occur. In this transformation, the chiral-bridged phosphoramidite ligand L3 shows some advantages in enantioselective control compared to its BINOL-derived counterpart.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo01771d