Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2021-12-03 DOI:10.1021/acs.orglett.1c03796

Jie Li, Pei Zhao, Ruoling Li, Wen Yang*, Wanxiang Zhao*

引用次数: 3

Abstract

An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B₂pin₂) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile carbon–boron bond transformations, were readily converted into diverse synthetically useful molecules, including α-hydroxy ketones, functionalized SEEs, and gem-difunctionalized aldehydes.

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铑催化硅烯醇醚的β-脱氢硼化反应:获得高功能化烯醇酯

公开了一种有效的铑催化乙醛衍生硅烯醇醚(SEEs)与双(pinacolato)二硼(B2pin2)的β-脱氢硼化反应。烷基取代和芳基取代的硅烯醇化反应进行得很顺利，提供了一系列有价值的功能化β-硼基硅烯醇酯，效率高，立体选择性好。此外，硼化产物通过多用途的碳硼键转化，很容易转化为各种合成有用的分子，包括α-羟基酮、功能化see和宝石二功能化醛。

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.