What does this research mean for the field?

Palladium-catalyzed asymmetric tandem allylation/cyclization of ortho-alkynylbenzaldehydes with allyltrimethylsilane provides access to chiral 1-allyl-1H-isochromenes with yields up to 82% and enantiomeric excess up to 97%. Novelty: ClaimNovelty.NOVEL_FINDING. Consensus alignment: ConsensusAlignment.NEUTRAL.

What question did this study set out to answer?

The aim is to develop a palladium-catalyzed method for synthesizing chiral isochromenes from alkynylbenzaldehydes.

February 26, 2026Organic Letters0 citations

Palladium-Catalyzed Enantioselective Tandem Allylation/Cyclization of ortho -Alkynylbenzaldehydes with Allyltrimethylsilane: Access to Chiral 1-Allyl-1 H -isochromenes

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MWM. Wang LLLing Li LZlinchun Zhang

Key Points

The aim is to develop a palladium-catalyzed method for synthesizing chiral isochromenes from alkynylbenzaldehydes.
Utilized palladium(II) complex with ligands and Lewis acids.
Performed asymmetric Sakurai–Hosomi-type reactions.
Combined alkynylbenzaldehydes with allyltrimethylsilane.
Achieved multiple product syntheses in a single reaction.
Produced 1-allyl-1H-isochromenes in yields up to 82%.
Achieved enantiomeric excess of 97%.
Demonstrated practicality with 22 different examples of product synthesis.

Abstract

Herein, we report the first palladium-catalyzed asymmetric Sakurai–Hosomi-type tandem allylation/cyclization of ortho-alkynylbenzaldehydes with allyltrimethylsilane. A chiral Pd(II)/L11 complex combined with ZnCl2 and Cu(OAc)2 afforded 1-allyl-1H-isochromenes (22 examples) in up to 82% yield and 97% ee. This protocol provides a concise, efficient, and practical route to chiral isochromene scaffolds of biological significance.

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Cite This Study

Wang et al. (2026) studied this question.

synapsesocial.com/papers/699fe3f995ddcd3a253e8131 https://doi.org/10.1021/acs.orglett.6c00112

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February 26, 2026Organic Letters0 citations

Palladium-Catalyzed Enantioselective Tandem Allylation/Cyclization of ortho -Alkynylbenzaldehydes with Allyltrimethylsilane: Access to Chiral 1-Allyl-1 H -isochromenes

View Full Paper

MWM. Wang LLLing Li LZlinchun Zhang

Key Points

The aim is to develop a palladium-catalyzed method for synthesizing chiral isochromenes from alkynylbenzaldehydes.
Utilized palladium(II) complex with ligands and Lewis acids.
Performed asymmetric Sakurai–Hosomi-type reactions.
Combined alkynylbenzaldehydes with allyltrimethylsilane.
Achieved multiple product syntheses in a single reaction.
Produced 1-allyl-1H-isochromenes in yields up to 82%.
Achieved enantiomeric excess of 97%.
Demonstrated practicality with 22 different examples of product synthesis.

Abstract

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Cite This Study

Wang et al. (2026) studied this question.

synapsesocial.com/papers/699fe3f995ddcd3a253e8131 https://doi.org/10.1021/acs.orglett.6c00112

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View Full Paper