Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold
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 (<i>R</i>)-<b>1</b> was s...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/19/4539 |
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| author | Hiroto Uno Kohei Matsuzaki Motoo Shiro Norio Shibata |
| author_facet | Hiroto Uno Kohei Matsuzaki Motoo Shiro Norio Shibata |
| author_sort | Hiroto Uno |
| collection | DOAJ |
| description | 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 (<i>R</i>)-<b>1</b> was synthesized from (<i>R</i>)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (<i>R</i>)-<b>1</b> worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (<i>R</i>)-<b>1</b> as a catalyst to evaluate the asymmetric induction. |
| first_indexed | 2024-03-10T15:52:04Z |
| format | Article |
| id | doaj.art-c09bd20a3d3a472cba9445989c178f58 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:52:04Z |
| publishDate | 2020-10-01 |
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| series | Molecules |
| spelling | doaj.art-c09bd20a3d3a472cba9445989c178f582023-11-20T16:00:00ZengMDPI AGMolecules1420-30492020-10-012519453910.3390/molecules25194539Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl ScaffoldHiroto Uno0Kohei Matsuzaki1Motoo Shiro2Norio Shibata3Department of Nanopharmaceutical Sciences, Nagoya, Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, JapanDepartment of Nanopharmaceutical Sciences, Nagoya, Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, JapanRigaku Corporation, 3-9-12, Matsubara-cho, Akishima-shi, Tokyo 196-8666, JapanDepartment of Nanopharmaceutical Sciences, Nagoya, Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, JapanThe 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 (<i>R</i>)-<b>1</b> was synthesized from (<i>R</i>)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (<i>R</i>)-<b>1</b> worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (<i>R</i>)-<b>1</b> as a catalyst to evaluate the asymmetric induction.https://www.mdpi.com/1420-3049/25/19/4539halogen-bondchiral halogen-bond donorLewis acidorgano-catalyst |
| spellingShingle | Hiroto Uno Kohei Matsuzaki Motoo Shiro Norio Shibata Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold Molecules halogen-bond chiral halogen-bond donor Lewis acid organo-catalyst |
| title | Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold |
| title_full | Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold |
| title_fullStr | Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold |
| title_full_unstemmed | Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold |
| title_short | Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp<sup>3</sup>-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold |
| title_sort | design and synthesis of a chiral halogen bond donor with a sp sup 3 sup hybridized carbon iodine moiety in a chiral fluorobissulfonyl scaffold |
| topic | halogen-bond chiral halogen-bond donor Lewis acid organo-catalyst |
| url | https://www.mdpi.com/1420-3049/25/19/4539 |
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