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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Spirocyclic Oxindole and Dihydrobenzofuran Formation via a Dearomative Cyclization-Nucleophilic Trapping Sequence
Bing-Xia Wang1, Bin-Xiang Yang1, Bao-Yu Du1
1College of Chemical Engineering, State Key Laboratory of Advanced Separation Membrane Materials, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.
None:
Dearomative difunctionalization of heteroarenes represents a convenient method toward heteroalicyclic compounds by breaking the aromaticity and forming two chemical bonds in a single step. Herein, a palladium-catalyzed alkenyletherification of indoles is disclosed through dearomative spirocyclization of C3-alkyne-tethered indoles, followed by intermolecular nucleophilic addition of the generated iminium with MeOH, affording a series of spirooxindoles in moderate to good yields after an additional oxidation. In addition, dearomative alkenylacetoxylation of C3-alkyne-tethered benzofurans with AcOH is also achieved toward spirodihydrobenzofurans in moderate to excellent yields. Preliminary exploration of the asymmetric version and synthetic transformation of the product are investigated.
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Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...