试剂控制的 Achmatowicz 产物与亲核试剂的区域发散环加成：双环[环戊[]吡喃和 8-氧杂双环[3.2.1]辛烷衍生物的合成。
Reagent-Controlled Regiodivergent Annulations of Achmatowicz Products with Vinylogous Nucleophiles: Synthesis of Bicyclic Cyclopenta[]pyrans and 8-Oxabicyclo[3.2.1]octane Derivatives.
机构信息
Department of Chemistry, National Chung Hsing University, Taichung City 40227, Taiwan, Republic of China.
出版信息
Org Lett. 2022 Oct 28;24(42):7806-7811. doi: 10.1021/acs.orglett.2c03127. Epub 2022 Oct 19.
Two reagent-controlled regiodivergent annulation protocols for Achmatowicz products with vinylogous nucleophiles have been developed, which furnished a series of bicyclic cyclopenta[]pyrans and 8-oxabicyclo[3.2.1]octane derivatives in 28-90% yields. Plausible mechanisms were proposed to involve either Pd-catalyzed Tsuji-Trost allyl-allyl coupling and concomitant Michael cyclization or quinine-promoted cascade stepwise [5 + 2] cycloaddition and intramolecular Michael cyclization.
已经开发出两种试剂控制的区域选择性环合协议，用于具有烯丙基亲核试剂的 Achmatowicz 产物，这两种协议以 28-90%的收率提供了一系列双环环戊[]吡喃和 8-氧杂双环[3.2.1]辛烷衍生物。提出了合理的机制，涉及 Pd 催化的 Tsuji-Trost 烯丙基-烯丙基偶联和伴随的迈克尔环化，或者奎宁促进的级联分步[5 + 2]环加成和分子内迈克尔环化。
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