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

Herein, we report the first palladium-catalyzed asymmetric Sakurai-Hosomi-type tandem allylation/cyclization of <i>ortho</i>-alkynylbenzaldehydes with allyltrimethylsilane. A chiral Pd(II)/<b>L11</b> complex combined with ZnCl<sub>2</sub> and Cu(OAc)<sub>2</sub> afforded 1-allyl-1<i>H</i>-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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Journal
Organic Letters
Published
2026-02-24
DOI
https://doi.org/10.1021/acs.orglett.6c00112
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

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

Ruifeng Fan, Zhenxiu He, Ponnam Devendar, linchun Zhang et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

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

Ruifeng Fan, Zhenxiu He, Ponnam Devendar, linchun Zhang, Meiqi Liang, M. Wang, Baomin Fan
article en

Abstract

Herein, we report the first palladium-catalyzed asymmetric Sakurai-Hosomi-type tandem allylation/cyclization of <i>ortho</i>-alkynylbenzaldehydes with allyltrimethylsilane. A chiral Pd(II)/<b>L11</b> complex combined with ZnCl<sub>2</sub> and Cu(OAc)<sub>2</sub> afforded 1-allyl-1<i>H</i>-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.

Organic LettersVol. 28(9)
Minzu University of China (CN)
Openalex Percentile: Top 43%
Catalytic C–H Functionalization Methods
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