Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ‑Butyrolactam

A palladium-catalyzed asymmetric chlorocyclization of\n1,6-enynes\nhas been described. Controlling the chloride ion concentration in\nthe system by substrate design is the key to achieving asymmetric\nchlorinated cyclization. In the presence of Pd(PhCN)<sub>2</sub>Cl<sub>2</sub> and chiral phosphoramidite ligands, the reaction accesses\ndiverse chiral (<i>E</i>)-α-chloromethylene-γ-butyrolactams\nwith excellent <i>E</i> selectivity and enantioselectivity.\nThe strategy features simple operations and mild conditions, offering\na practical and reliable route for the synthesis of chiral butyrolactam\ncompounds.

Publication Details

Journal
Figshare
Published
2024-12-25
DOI
https://doi.org/10.1021/acs.joc.4c02477.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
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article
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article

Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ‑Butyrolactam

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Mycorrhizal Fungi and Plant Interactions
article

Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ‑Butyrolactam

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Abstract

A palladium-catalyzed asymmetric chlorocyclization of\n1,6-enynes\nhas been described. Controlling the chloride ion concentration in\nthe system by substrate design is the key to achieving asymmetric\nchlorinated cyclization. In the presence of Pd(PhCN)<sub>2</sub>Cl<sub>2</sub> and chiral phosphoramidite ligands, the reaction accesses\ndiverse chiral (<i>E</i>)-α-chloromethylene-γ-butyrolactams\nwith excellent <i>E</i> selectivity and enantioselectivity.\nThe strategy features simple operations and mild conditions, offering\na practical and reliable route for the synthesis of chiral butyrolactam\ncompounds.

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Mycorrhizal Fungi and Plant Interactions
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Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ‑Butyrolactam · Figshare (2024) | TGRS Research Map | TGRS