Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone,Chemistry - An Asian Journal

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Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2020-10-14 , DOI: 10.1002/asia.202001102
Tomoki Ura ₁ , Daisuke Shimbo ₁ , Masaharu Yudasaka ₁ , Norihiro Tada ₁ , Akichika Itoh ₁

Affiliation

The stereoselective synthesis of cis‐β‐phenoxyvinyl benziodoxolones (cis‐β‐phenol‐VBXs) from an ethynyl benziodoxolone‐acetonitrile complex (EBX‐MeCN) and various phenols is reported herein. The reaction tolerates different phenol derivatives, including complex natural products, and can be conducted under mild conditions. The synthesis was performed in an aqueous solvent in the absence and presence of a catalytic amount of a base. Selectively mono‐ and di‐deuterated cis‐β‐phenol‐VBXs were also prepared. cis‐β‐Phenol‐VBXs were stereospecifically derivatized to cis‐alkynylvinyl ethers and cis‐iodovinyl ethers without loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

中文翻译：

乙炔基苯并恶唑啉酮合成苯酚衍生的顺式乙烯基醚

的立体选择性合成顺式- β -phenoxyvinyl benziodoxolones（顺式- β -苯酚-VBXs）从benziodoxolone -乙腈络合物（EBX-MeCN中）和各种苯酚在本文中报道的乙炔基。该反应耐受不同的苯酚衍生物，包括复杂的天然产物，并且可以在温和的条件下进行。在不存在和存在催化量的碱的情况下，在水性溶剂中进行合成。选择性单和二氘代顺- β -苯酚，VBXs还准备。顺式-β-苯酚-VBXs立体定向衍生为顺式-炔基乙烯基醚和顺式碘乙烯基醚，而不会失去立体选择性或降低氘/氢比。

更新日期：2020-12-01

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