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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
MULTICOMPONENT REACTIONS: SYNTHESIS OF SPIROCYCLIC TETRAHYDROPYRAN DERIVATIVES BY PRINS CYCLIZATION
Arun K Ghosh1, Dongwoo Shin1, Gary Schiltz1
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA; arunghos@uic.edu.
Abstract:
Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.
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