首页> 外文期刊>Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry >Diastereoselective synthesis of quinolizidin-4-one and indolizidin-3-one derivatives with a spirocyclic motif via cascade cyclization using a gold(I)/Bronsted acid relay catalysis
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Diastereoselective synthesis of quinolizidin-4-one and indolizidin-3-one derivatives with a spirocyclic motif via cascade cyclization using a gold(I)/Bronsted acid relay catalysis

机译:通过使用金(I)/布朗斯台德酸中继催化的级联环化反应,非对映选择性合成具有螺环基序的喹诺齐丁-4-酮和吲哚齐丁-3-酮衍生物

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Functionalized quinolizidin-4-ones and indolizidin-3-ones were synthesized from mixed N,O-acetals with a terminal alkyne unit and nucleophiles with two reactive sites by a gold(I)/Bronsted acid relay catalysis with 40-90% yield. The reactions are proposed to proceed through gold-catalyzed carboalkoxylation of the alkynes with the internal mixed N,O-acetals, giving the corresponding cyclic enols, which are transformed to spirocyclic compounds by a Bronsted acid catalyst. The latter spirocyclization process occurs under thermodynamic control, providing polycyclic quinolizidin-4-one and indolizidin-3-one derivatives diastereoselectively. (C) 2015 Elsevier Ltd. All rights reserved.
机译:由具有末端炔单元的N,O-乙缩醛和具有两个反应位点的亲核试剂通过金(I)/布朗斯台德酸中继催化合成功能化的喹啉zidin-4-ones和indolizidin-3-ones,产率为40-90%。建议该反应通过炔烃与内部混合的N,O-乙缩醛的金催化的碳烷氧基化反应进行,得到相应的环状烯醇,并通过布朗斯台德酸催化剂将其转化为螺环化合物。后者的螺环化过程是在热力学控制下发生的,非对映选择性地提供了多环喹喔啉-4-酮和吲哚齐丁-3-酮衍生物。 (C)2015 Elsevier Ltd.保留所有权利。

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