Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols

Abstract The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized ( Z )-allyl alcohols in mostly good yields is reported. Benzo[ d ]isoxazoles were found to be excellent building blocks for th...

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Bibliographic Details
Published in:Synlett 2019-07, Vol.30 (11), p.1339-1345
Main Authors: Chen, Zhiyuan, Wu, Wenjin, Zheng, Tiantian, Tan, Jie, Pu, Shouzhi
Format: Article
Language:English
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Summary:Abstract The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized ( Z )-allyl alcohols in mostly good yields is reported. Benzo[ d ]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile source for the preparation of organonitrile derivatives. Silver salt combined with gold catalyst were found to be necessary for the success of this transformation.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1611828