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

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 chi...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2023-11, Vol.88 (22), p.15658-15665
Main Authors: Chao, Yang, Subramaniam, Muthusamy, Namitharan, Kayambu, Zhu, Yumei, Koolma, Victor, Hao, Zitong, Li, Shikang, Wang, Yaxin, Hudoynazarov, Ilyos, Miloserdov, Fedor M., Zuilhof, Han
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01656