Palladium-CatalyzedEnantioselective Tandem Phosphinolation/Cyclizationof <i>ortho</i>-Alkynylbenzaldehydes and H‑PhosphineOxides: Access to C1-Phosphinoylated 1<i>H</i>‑Isochromenes

A novel and effective method for the synthesis of chiral C1-phosphinoylated 1<i>H</i>-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)<sub>2</sub>, a Josiphos-based ligand <b>L9</b>, and ZnCl<sub>2</sub> in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).

Publication Details

Journal
Figshare
Published
2025-03-22
DOI
https://doi.org/10.1021/acs.orglett.5c00757.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-CatalyzedEnantioselective Tandem Phosphinolation/Cyclizationof ortho-Alkynylbenzaldehydes and H‑PhosphineOxides: Access to C1-Phosphinoylated 1H‑Isochromenes

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Catalytic C–H Functionalization Methods
article

Palladium-CatalyzedEnantioselective Tandem Phosphinolation/Cyclizationof ortho-Alkynylbenzaldehydes and H‑PhosphineOxides: Access to C1-Phosphinoylated 1H‑Isochromenes

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Abstract

A novel and effective method for the synthesis of chiral C1-phosphinoylated 1<i>H</i>-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)<sub>2</sub>, a Josiphos-based ligand <b>L9</b>, and ZnCl<sub>2</sub> in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).

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Catalytic C–H Functionalization Methods
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Palladium-CatalyzedEnantioselective Tandem Phosphinolation/Cyclizationof <i>ortho</i>-Alkynylbenzaldehydes and H‑PhosphineOxides: Access to C1-Phosphinoylated 1<i>H</i>‑Isochromenes · Figshare (2025) | TGRS Research Map | TGRS