Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes

A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses of (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, the reaction involves a phosphine-cata...

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Bibliographic Details
Published in:Organic letters 2016-06, Vol.18 (12), p.2954-2957
Main Authors: Zhou, Qing-Fa, Zhang, Kui, Cai, Lingchao, Kwon, Ohyun
Format: Article
Language:English
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Summary:A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses of (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, the reaction involves a phosphine-catalyzed Michael addition of an alkylideneazinate and rearrangement of the cyclic nitronate to the α-nitrosodihydrofuran.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01299