Proton Relay Catalysis Enables the Synthesis of 2-Oxa- and 2-Azabicyclo[2.2.1]heptanes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-12 DOI:10.1021/acs.orglett.5c01962

Chenyang Chang, Stephanie G. E. Amos, Jordi Benet-Buchholz, Arjan W. Kleij

引用次数: 0

Abstract

An effective binary catalytic system enables the synthesis of oxa- and aza-bicyclo[2.2.1]heptanes from cyclic γ-epoxy-alcohols. A combination of an aminotriphenolate Al(III) complex and a bromide salt delivers a wide variety of target compounds in good to excellent yields, with high diastereo-control. The mechanism includes a double-nucleophilic displacement at a carbon center via a proton-relay step involving the Al(III) complex phenolate, as supported by control experiments. Med-chem inspired synthons could successfully be obtained with the aza-bicyclo[2.2.1]heptanes.

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质子接力催化合成2-氧-和2-氮杂环[2.2.1]庚烷

以环γ-环氧醇为原料，建立了一种有效的二元催化体系，可合成氧-和氮-双环[2.2.1]庚烷。氨基三酚酸铝（III）配合物和溴化盐的组合提供了各种各样的目标化合物，具有良好的收率到优异的收率，具有高的非对映控制。该机制包括碳中心的双亲核位移，通过涉及Al（III）配合酚酸盐的质子接力步骤，如控制实验所支持的。以杂氮-双环[2.2.1]庚烷为原料，成功地获得了受药物化学启发的合成子。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.