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Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
Organic Letters ( IF 4.9 ) Pub Date : 2021-12-03 , DOI: 10.1021/acs.orglett.1c03796
Jie Li 1 , Pei Zhao 1 , Ruoling Li 1 , Wen Yang 1 , Wanxiang Zhao 1
Affiliation  

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.

中文翻译:

铑催化的甲硅烷醇醚的 β-脱氢硼酰化:获得高度官能化的烯醇化物

公开了醛衍生的甲硅烷基烯醇醚(SEE)与双(频哪醇)二硼(B 2 pin 2 )的有效铑催化的β-脱硼氢化。硼基化反应与烷基和芳基取代的 SEE 进行得很好,提供了一系列有价值的功能化 β-硼基甲硅烷基烯醇化物,具有高效率和优异的立体选择性。此外,borylated产品,通过通用的碳-硼键的变换,被容易地转化为合成多样有用分子,包括α羟基酮,官能看到,和宝石-difunctionalized醛。
更新日期:2021-12-17
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