Selective Cascade Reaction of Bisallenes via Palladium‐Catalyzed Aerobic Oxidative Carbocyclization–Borylation and Aldehyde Trapping

A cascade reaction, consisting of a palladium‐catalyzed regioselective aerobic oxidative carbocyclization–borylation of bisallenes and a final aldehyde trapping, afforded triene alcohols with high diastereoselectivity. The cascade reaction occurs under mild reaction conditions and proceeds via an al...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (6), p.1590-1594
Main Authors: Naidu, Veluru Ramesh, Posevins, Daniels, Volla, Chandra M. R., Bäckvall, Jan‐E.
Format: Article
Language:English
Subjects:
Alcohols
biomimetic oxidation
bisallene
Cascade chemical reactions
cascade reaction
catalysis
Organic Chemistry
organisk kemi
Palladium
Trapping
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Summary:A cascade reaction, consisting of a palladium‐catalyzed regioselective aerobic oxidative carbocyclization–borylation of bisallenes and a final aldehyde trapping, afforded triene alcohols with high diastereoselectivity. The cascade reaction occurs under mild reaction conditions and proceeds via an allylboron intermediate that is trapped by the aldehyde in a stereoselective manner. Efficient cascade: A palladium‐catalyzed regioselective aerobic oxidative carbocyclization–borylation of bisallenes generates a reactive allylboron intermediate that is trapped by aldehyde present in the reaction mixture. The cascade reaction proceeds with high diastereoselectivity.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201610524