Enantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-28 Epub Date: 2025-02-14 DOI:10.1021/acs.orglett.5c00107

Wenke Dong, Zheming Liu, Anbang Bai, Xiaoyu Zhang, Peiwen Han, Jingyi He, Chenchen Li

引用次数: 0

Abstract

Heteroatomic groups in alkenes typically direct thermodynamically favored chain walking of C═C bonds toward themselves, thereby facilitating C-H bond functionalization near the heteroatoms. We present herein an efficient cobalt-catalyzed contra-thermodynamic remote hydroboration of alkenylboronates with pinacolborane to synthesize chiral 1,n-diboronates. This protocol features a broad substrate scope, high functional group tolerance, and excellent enantioselectivity. Mechanistic studies indicate the involvement of a chain-walking process. Gram-scale reactions and various product derivatizations further highlight its practicality.

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对映选择性钴催化硼烯基酸酯的远程硼氢化反应。

烯烃中的杂原子基团通常在热力学上引导C = C键向自身走链，从而促进C- h键在杂原子附近的功能化。本文提出了一种高效的钴催化的溴烯基硼酸酯与蒎烷硼烷的反热力学远程硼氢化反应，以合成手性1，n-二硼酸酯。该方案具有广泛的底物范围，高官能团耐受性和出色的对映体选择性。机械学研究表明，这与链式行走过程有关。克级反应和各种产品衍生化进一步凸显了它的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.