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通过环醚化和克莱森重排合成八元环胺的策略。

A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.

机构信息

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.

Chemical Kinomics Research Center, KIST and Division of Bio-Medical Science & Technology, KIST-School UST, 5, Hwarangro 14-gil, Seongbuk-gu, Seoul, 02792, Republic of Korea.

出版信息

Org Lett. 2021 May 7;23(9):3300-3303. doi: 10.1021/acs.orglett.1c00763. Epub 2021 Apr 12.

Abstract

Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This operationally simple reaction is tolerant of many functional groups and applicable to the synthesis of various medium-sized ring nitrogen-containing heterocycles.

摘要

八元氮杂环化合物可由镍催化的环醚化反应和随后的仲醇和叔醇的克莱森重排反应直接合成。特别是,叔醇可通过一锅法转化以中等至良好的收率得到目标产物。该反应操作简单,对许多官能团具有容忍性,适用于各种中氮杂环的合成。

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