铜（II）催化二氮嘧啶与氧环烷的不对称（3+3）环化反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-29 DOI:10.1021/acs.orglett.5c0006410.1021/acs.orglett.5c00064

Ying Hu, Heng-Bin Yu, Yin Tian*, Ming-Sheng Xie* and Hai-Ming Guo*,

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引用次数: 0

摘要

在10 mol %的手性铜（II）配合物催化下，在温和的反应条件下，通过C-N键裂解，实现了二氮吡啶与氧环的高度不对称（3+3）环。以Cu(OTf)2为Lewis酸，c1对称咪唑烷-吡咯咪唑酮吡啶为配体，通过形成立体定向的C-N / C-O键，得到了多种四氢-[1,3,4]-恶二嗪类化合物，产率中~高（产率高达93%），非映体选择性（>20:1 dr）和对映体选择性（高达92% ee）。通过DFT计算，建立了催化循环和立体化学模型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes

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Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes

Highly asymmetric (3+3) annulation of diaziridines with oxiranes via C–N bond cleavage in diaziridine was achieved under 10 mol % of chiral copper(II) complex as the catalyst under mild reaction conditions. With Cu(OTf)₂ as the Lewis acid and C₁-symmetric imidazolidine-pyrroloimidazolone pyridine as the ligand, diverse tetrahydro-[1,3,4]-oxadiazines were obtained by stereospecific C–N/C–O bond formation in moderate to good yields (up to 93% yield) and high diastereo- (>20:1 dr) and enantioselectivities (up to 92% ee). The catalytic cycle and stereochemical model were proposed by DFT calculation.

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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.