Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold

The first example of a chiral halogen-bond donor with a sp(3)-hybridized carbon–iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from (R)-1,1′-binaphthol in 11 steps. An NMR tit...

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Autores principales: Uno, Hiroto, Matsuzaki, Kohei, Shiro, Motoo, Shibata, Norio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7583727/
https://www.ncbi.nlm.nih.gov/pubmed/33022984
http://dx.doi.org/10.3390/molecules25194539
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author Uno, Hiroto
Matsuzaki, Kohei
Shiro, Motoo
Shibata, Norio
author_facet Uno, Hiroto
Matsuzaki, Kohei
Shiro, Motoo
Shibata, Norio
author_sort Uno, Hiroto
collection PubMed
description The first example of a chiral halogen-bond donor with a sp(3)-hybridized carbon–iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from (R)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (R)-1 worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (R)-1 as a catalyst to evaluate the asymmetric induction.
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spelling pubmed-75837272020-10-28 Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold Uno, Hiroto Matsuzaki, Kohei Shiro, Motoo Shibata, Norio Molecules Article The first example of a chiral halogen-bond donor with a sp(3)-hybridized carbon–iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from (R)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (R)-1 worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (R)-1 as a catalyst to evaluate the asymmetric induction. MDPI 2020-10-03 /pmc/articles/PMC7583727/ /pubmed/33022984 http://dx.doi.org/10.3390/molecules25194539 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Uno, Hiroto
Matsuzaki, Kohei
Shiro, Motoo
Shibata, Norio
Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title_full Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title_fullStr Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title_full_unstemmed Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title_short Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp(3)-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
title_sort design and synthesis of a chiral halogen-bond donor with a sp(3)-hybridized carbon–iodine moiety in a chiral fluorobissulfonyl scaffold
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7583727/
https://www.ncbi.nlm.nih.gov/pubmed/33022984
http://dx.doi.org/10.3390/molecules25194539
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