Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold

Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold

<b> </b>The first example of a chiral halogen-bond donor with a sp<sup>3</sup>-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...

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Bibliographic Details
Main Authors: Hiroto Uno, Kohei Matsuzaki, Motoo Shiro, Norio Shibata
Format: Article
Language:English
Published: MDPI AG 2020-10-01
Series:Molecules
Subjects:
halogen-bond
chiral halogen-bond donor
Lewis acid
organo-catalyst
Online Access:https://www.mdpi.com/1420-3049/25/19/4539
Description
Summary:<b> </b>The first example of a chiral halogen-bond donor with a sp<sup>3</sup>-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.
ISSN:1420-3049

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