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

[Image: see text] 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 b...

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Autores principales: Chao, Yang, Subramaniam, Muthusamy, Namitharan, Kayambu, Zhu, Yumei, Koolma, Victor, Hao, Zitong, Li, Shikang, Wang, Yaxin, Hudoynazarov, Ilyos, Miloserdov, Fedor M., Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10660663/
https://www.ncbi.nlm.nih.gov/pubmed/37903243
http://dx.doi.org/10.1021/acs.joc.3c01656
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author Chao, Yang
Subramaniam, Muthusamy
Namitharan, Kayambu
Zhu, Yumei
Koolma, Victor
Hao, Zitong
Li, Shikang
Wang, Yaxin
Hudoynazarov, Ilyos
Miloserdov, Fedor M.
Zuilhof, Han
author_facet Chao, Yang
Subramaniam, Muthusamy
Namitharan, Kayambu
Zhu, Yumei
Koolma, Victor
Hao, Zitong
Li, Shikang
Wang, Yaxin
Hudoynazarov, Ilyos
Miloserdov, Fedor M.
Zuilhof, Han
author_sort Chao, Yang
collection PubMed
description [Image: see text] 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.
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spelling pubmed-106606632023-11-21 Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions Chao, Yang Subramaniam, Muthusamy Namitharan, Kayambu Zhu, Yumei Koolma, Victor Hao, Zitong Li, Shikang Wang, Yaxin Hudoynazarov, Ilyos Miloserdov, Fedor M. Zuilhof, Han J Org Chem [Image: see text] 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. American Chemical Society 2023-10-30 /pmc/articles/PMC10660663/ /pubmed/37903243 http://dx.doi.org/10.1021/acs.joc.3c01656 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Chao, Yang
Subramaniam, Muthusamy
Namitharan, Kayambu
Zhu, Yumei
Koolma, Victor
Hao, Zitong
Li, Shikang
Wang, Yaxin
Hudoynazarov, Ilyos
Miloserdov, Fedor M.
Zuilhof, Han
Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title_full Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title_fullStr Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title_full_unstemmed Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title_short Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
title_sort synthesis of large macrocycles with chiral sulfur centers via enantiospecific sufex and suphenex click reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10660663/
https://www.ncbi.nlm.nih.gov/pubmed/37903243
http://dx.doi.org/10.1021/acs.joc.3c01656
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