Maqola

Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions

Yang ChaoSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, ChinaMuthusamy SubramaniamLaboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The NetherlandsKayambu NamitharanLaboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The NetherlandsYumei ZhuSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, ChinaVictor KoolmaLaboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The NetherlandsZitong HaoSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, ChinaShangru LiSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, ChinaYaxin WangSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, ChinaIlyos HudoynazarovDivision of Organic Synthesis and Applied Chemistry, National University of Uzbekistan, Tashkent 100174, UzbekistanFedor M. MiloserdovLaboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The NetherlandsHan ZuilhofLaboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The Netherlands

The Journal of Organic Chemistryjournal2023en

ABI

Annotatsiya

Here we report the first asymmetric synthesis of large chiral macrocycles with chiral sulfur atoms. Building on stereospecific SuFEx and SuPhenEx click chemistries, this approach utilizes disulfonimidoyl fluorides and disulfonimidoyl p-nitrophenolates─which are efficient building blocks with two chiral sulfur centers, and diphenols to efficiently form novel S–O bonds. Characteristic results include the enantiospecific one-step synthesis of rings consisting of 21–58 members and characterization of both enantiomers (R,R and S,S) by e.g. X-ray crystallography.

Hali tarjima qilinmagan

Mavzular

Synthesis and Catalytic Reactions Sulfur-Based Synthesis Techniques Click Chemistry and Applications

Identifikatorlar

DOI: 10.1021/acs.joc.3c01656

Iqtiboslar va manbalar

0 ta iqtibos77 ta foydalanilgan manba

Koʻrsatkichlar — AkademScholar · Tez orada