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钯催化γ-亚甲基-δ-戊内酯与异吲哚酮的脱羧环化反应立体选择性合成螺环氧化吲哚

Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins.

作者信息

Shintani Ryo, Hayashi Shin-ya, Murakami Masataka, Takeda Momotaro, Hayashi Tamio

机构信息

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

出版信息

Org Lett. 2009 Aug 20;11(16):3754-6. doi: 10.1021/ol901348f.

Abstract

A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described.

摘要

通过γ-亚甲基-δ-戊内酯与异吲哚酮的钯催化脱羧环化反应,开发了一种新型螺环氧化吲哚衍生物的合成方法。通过使用新制备的亚磷酰胺配体,反应顺利进行,具有优异的非对映选择性。还描述了其使用手性亚磷酰胺配体应用于不对称催化的初步结果。

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