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通过钯催化的芳基烯丙基环化级联反应实现立体选择性螺环内酰胺合成。

Stereoselective spirolactam synthesis via palladium catalyzed arylative allene carbocyclization cascades.

机构信息

Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom.

出版信息

Org Lett. 2010 Sep 3;12(17):3784-7. doi: 10.1021/ol101425y.

Abstract

A diastereoselective arylative carbocyclization of pro-nucleophile-linked allenes with aryl and heteroaryl halides to provide spirocyclic lactam products with moderate to high diastereoselectivities and good yields under Pd(0) catalysis is reported. Being operationally simple and tolerant of multiple points of diversity, this complexity building reaction cascade, in which two new carbon-carbon bonds and one new heterocyclic ring are created, should be of high value in both complex natural product synthesis as well as compound library synthesis.

摘要

报道了在钯(0)催化下,通过前亲核体连接的丙二烯与芳基和杂芳基卤化物的非对映选择性芳基环化反应,以中等至较高的非对映选择性和良好的收率得到螺环内酰胺产物。这种复杂的构建反应级联反应操作简单,对多个多样性点具有耐受性,其中形成了两个新的碳-碳键和一个新的杂环,在复杂天然产物合成以及化合物库合成中都具有很高的价值。

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