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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Ipso-Cyclization via a Dienone-Phenol Rearrangement of Alkynyloxy Cyclohexadienones for the Synthesis of
Archana Rai1,2, Ananya I Kundu1, Ekta Shukla1
1Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
Abstract:
Herein, we present a convenient method to access oxaspiro[4.5]trienone compounds from alkynyloxy cyclohexadienones. The reactions are catalyzed by Lewis/Bronsted acids, yielding the desired products in moderate to good yields under very mild reaction conditions. The process, which involves a dienone-phenol rearrangement, is characterized by its simplicity and the absence of any additional activators. The synthesis of the oxaspiro[4.5]trienone compounds is amenable to gram-scale reactions along with subsequent product transformations, making this approach practical and attractive.
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