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Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp3-Hybridized Carbon-Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold.

ABSTRACT: The first example of a chiral halogen-bond donor with a sp3-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.

SUBMITTER: Uno H

PROVIDER: S-EPMC7583727 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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

Uno Hiroto H Matsuzaki Kohei K Shiro Motoo M Shibata Norio N

Molecules (Basel, Switzerland) 20201003 19

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 asymmetr ...[more]

PMID: 33022984

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