Gold(I)‐Catalyzed Synthesis of Six‐Membered P,O‐Heterocycles  via  Hydration/Intramolecular Cyclization Cascade Reaction | Zendy

Zhang Shan | Zendy; Cheng Haiyang | Zendy; Mo Sheng | Zendy; Yin Shiwei | Zendy; Zhang Zunting | Zendy; Wang Tao | Zendy

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Gold(I)‐Catalyzed Synthesis of Six‐Membered P,O‐Heterocycles via Hydration/Intramolecular Cyclization Cascade Reaction

Author(s) -

Zhang Shan,

Cheng Haiyang,

Mo Sheng,

Yin Shiwei,

Zhang Zunting,

Wang Tao

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201900605

Subject(s) - chemoselectivity , chemistry , intramolecular force , alkyne , cascade , catalysis , cascade reaction , density functional theory , combinatorial chemistry , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , chromatography

Herein, we report the synthesis of six‐membered P,O‐heterocycles from dialkynylphosphine oxides. By using gold(I) complexes, the chemoselectivity of the reaction was switched from literature‐reported double hydration to a hydration/intramolecular cyclization cascade. Control experiments indicated that the first alkyne hydration product is an intermediate of the reaction. In addition, a density functional theory (DFT) calculation allowed to rationalize the observed chemoselectivity.

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