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Abstract <p>The concise synthesis of novel monocarbamate-triacetate with a configuration like that of <i>cis-trans-cis</i>-cyclohexanetetrol is reported for the first time. Photooxygenation reaction of the starting compound cyclohexadiene gave the bicyclic endoperoxide compound. Controlled reduction of the endoperoxide with thiourea afforded the allylic <i>cis</i>-diol compound, and subsequent reaction of the <i>cis</i>-diol with two equivalents of <i>p</i>-TsNCO led to the formation of the key compound bis-carbamate. Treatment of the bis-carbamate compound with Pd<sub>2</sub>(dba)<sub>3</sub>·CHCl<sub>3</sub> in the presence of trimethylsilyl azide (TMSN<sub>3</sub>) produced a new monocarbamate compound as well as an oxazolidinone derivative. By oxidation of the double bond in the monocarbamate with osmium tetraoxide and subsequent acetylation with AcCl, a desired new monocarbamate triacetate compound was obtained.</p>

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Concise Synthesis of Monocarbamate-Cyclohexanetriacetate from Allylic Bis-Carbamate

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • L. Kelebekli

摘要

Abstract

The concise synthesis of novel monocarbamate-triacetate with a configuration like that of cis-trans-cis-cyclohexanetetrol is reported for the first time. Photooxygenation reaction of the starting compound cyclohexadiene gave the bicyclic endoperoxide compound. Controlled reduction of the endoperoxide with thiourea afforded the allylic cis-diol compound, and subsequent reaction of the cis-diol with two equivalents of p-TsNCO led to the formation of the key compound bis-carbamate. Treatment of the bis-carbamate compound with Pd2(dba)3·CHCl3 in the presence of trimethylsilyl azide (TMSN3) produced a new monocarbamate compound as well as an oxazolidinone derivative. By oxidation of the double bond in the monocarbamate with osmium tetraoxide and subsequent acetylation with AcCl, a desired new monocarbamate triacetate compound was obtained.