Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 15, Issue 23, Pages 4000-4004Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202001102
Keywords
hypervalent iodine compounds; vinyl ethers; phenols; stereoselective; deuterium
Categories
Funding
- JSPS KAKENHI [19K06977]
- SIS (The Society of Iodine Science)
- Grants-in-Aid for Scientific Research [19K06977] Funding Source: KAKEN
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The stereoselective synthesis of cis-beta-phenoxyvinyl benziodoxolones (cis-beta-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-beta-phenol-VBXs were also prepared. cis-beta-Phenol-VBXs were stereospecifically derivatized to cis-alkynylvinyl ethers and cis-iodovinyl ethers without loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.
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