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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Pd-Catalyzed Sequential Electrophilic Cyclization/Selective C-H Annulation Cascade: Synthesis of
Vavilapalli Suresh1,2, T Mahipal Reddy1,2, Dattatri1,2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
Harnessing the organo-palladium intermediates generated from electrophilic cyclizations for tandem C-C bond construction is a challenging task but constitutes an excellent tool for constructing complex motifs from simpler substrates. We realize herein such a cyclative annulation of alkynyl-oxime ethers with maleimides for the facile construction of isoxazole-phthalimide hybrid motifs through Pd(II) catalysis. This protocol features excellent regio-selectivity in C-H selection, a broad substrate scope, good functional group tolerance, and scalability. Necessary KIE & labeling studies give insight into the reaction mechanism.
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