Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone. Issue 23 (26th October 2020)

• Record Type: Journal Article
• Authors: Ura, Tomoki; Shimbo, Daisuke; Yudasaka, Masaharu; Tada, Norihiro; Itoh, Akichika
• Is Part Of: Chemistry, an Asian journal. Volume 15:Issue 23(2020)
• Page Start: 4000
• Page End: 4004
• Publication Date: 2020-10-26
• Subjects: hypervalent iodine compounds -- vinyl ethers -- phenols -- stereoselective -- deuterium; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202001102
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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. Abstract : Stereoselective synthesis of cis ‐ β ‐phenoxyvinyl benziodoxolones ( cis ‐ β ‐phenol‐VBXs) from an ethynyl benziodoxolone‐acetonitrile complex (EBX‐MeCN) and various phenols under mild conditions has been developed. Selective synthesis of di‐ and mono‐deuterated cis ‐ β ‐phenol‐VBXs was achieved by exchanging the acidic proton with deuterium. The preparation of phenol‐derived cis ‐alkynylvinyl ethers and cis ‐iodovinyl ethers was also conducted.