Dual In Situ Generation of Aliphatic Vinyl Ethers and Electron-Deficient ortho-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition: A Selective One-Pot Synthesis of 3-Alkylchromanes,Synlett

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Dual In Situ Generation of Aliphatic Vinyl Ethers and Electron-Deficient ortho-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition: A Selective One-Pot Synthesis of 3-Alkylchromanes
Synlett ( IF 1.7 ) Pub Date : 2020-05-06 , DOI: 10.1055/s-0040-1707522
Yujiro Hoshino ₁ , Kiyoshi Honda ₁ , Kenta Tanaka ₁ , Ko Ueno ₁ , Yuta Tanaka ₁ , Naoya Ohtsuka ₂ , Yosuke Asada ₁ , Mami Kishimoto ₁ , Shuto Sunaga ₁

Affiliation

An inverse-electron-demand [4+2] cycloaddition of in situ generated aliphatic vinyl ethers and electron-deficient ortho-quinone methides (o-QMs) has been developed. The reaction of in situ generated aliphatic vinyl ethers with o-QMs afforded the corresponding 3-alkylchromanes with high stereo- and regioselectivities. The method provides a versatile access to functionalized 3-alkylchromanes and it constitutes a useful tool for the synthesis of biologically active chromanes.

中文翻译：

用于逆电子需求 [4+2] 环加成的脂肪族乙烯基醚和缺电子邻醌甲基的双原位生成：3-烷基色烷的选择性一锅法合成

已经开发了原位生成的脂肪族乙烯基醚和缺电子邻醌甲基化物 (o-QMs) 的逆电子需求 [4+2] 环加成。原位生成的脂肪族乙烯基醚与 o-QM 的反应提供了相应的具有高立体选择性和区域选择性的 3-烷基色满。该方法提供了对官能化 3-烷基色满的通用途径，它构成了合成生物活性色满的有用工具。

更新日期：2020-05-06

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