Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Communications  

Yuuya Kawasaki, Kazunobu Igawa,Tomoya Hayashibara, Yuki Seto, Yutaro Taniguchi, Katsuhiko Tomooka

DOI： 10.1039/d3cc03023g

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DOI： org/10.1002/chir.23429

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Planar chiral oxa-[7]orthocyclophene 1a was designed and synthesized with two different synthetic routes. X-ray crystallo-graphic analyses of 1a and its platinum complex revealed a highly distorted ring structure and the absolute stereochemistry of 1a, respectively. Epoxidation and [2,3]-Wittig rearrangement of 1a provided with central chiral molecules, without the loss of enantiomeric purity.

DOI： 10.1246/cl.220219

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Newly synthesized ten-membered diallylic nitrogen cycle, having E- and Z-alkene moieties, shows labile planar-chirality at ambient temperature. VT-NMR experiments revealed the detail of the stereochemical behavior of interconversion of the enantiomers and diastereomers. In sharp contrast, Pt-complex of the nitrogen cycle have more stable planar chirality, and the enantiomers of the Pt-complex were isolated by HPLC using a chiral stationary phase.

DOI： 10.1246/cl.220143

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Chemical Communications  

Dynamic asymmetric induction (DYASIN) of racemic dynamic chiral heterohelicenes afforded their highly enantioenriched forms (up to 96% ep) in quantitative yields. These heterohelicenes were readily converted into semi-static axial-chiral 1,1′-binaphthyl derivatives in a stereospecific manner.

DOI： 10.1039/d1cc05881a

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

Aza-orthocyclophyne 3b with an oxy-substituent on the 16 position of the benzene ring was synthesized, and it was revealed that the stereochemical stability of 3b is consistent with the order of 1,3-steric repulsion between the C2 methylene protons and the oxy-substituent.

DOI： 10.3987/COM-22-S(R)18

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Language：Others   Publishing type：Research paper (scientific journal)  

An automated microflow measurement system for the kinetic study of racemization of dynamic chiral molecules was developed. This system facilitated the analysis of fast racemization within several seconds at elevated temperatures owing to its rapid heating ability, high performance for controlling short residence times, and ease of connection to HPLC systems for direct measurement of the enantiomeric purity. A more precise analysis was realized by combination of microflow and common batch measurements over a broad range of temperatures.

DOI： 10.1021/acs.joc.1c00914

Language：Others   Publishing type：Research paper (scientific journal)  

Copyright © 2020 American Chemical Society. The addition-type ozone oxidation of silylalkenes is a highly efficient reaction to provide synthetically versatile α-silylperoxy carbonyl compounds. To gain insight into the reaction mechanism, we performed a computational study, which revealed that the reaction proceeds via [1,2]-Brook rearrangement-type silyl migration of primary ozonide. In sharp contrast to the addition-type reactions, the ozone oxidation of α-alkoxysilylalkenes proceeds in a cleavage-type manner to afford excellent yields of silacarboxylic acid esters via the 1,3-cycloelimination of primary ozonide prior to 1,2-silyl migration.

DOI： 10.1021/acs.joc.9b03350

Language：Others   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/asia.202000042

Language：English   Publishing type：Research paper (scientific journal)  

Newly designed buckle units for copper-free click chemistry: 4,8-diazacyclononynes (DACNs) were efficiently synthesized with a one-pot procedure from commercially available 2-butyne-1,4-diol. The synthesized DACNs possess versatile connectors for the introduction of functional units and exhibit high click reactivity.

DOI： 10.1055/s-0036-1588839

Repository Public URL： https://hdl.handle.net/2324/7172102

Language：English   Publishing type：Research paper (scientific journal)  

Ozone oxidation of silyl-substituted alkenes, namely silylalkenes, proceeds in an addition-type manner to afford alpha-silylperoxy carbonyl compounds in good to excellent yields, without the formation of normal ozonolysis products. Herein the ozone oxidation of chiral alkenylsilanes prepared from alkynes and a newly designed chiral hydrosilane is reported. The reaction affords silylperoxides with high diastereoselectivity (up to 94% d.r.). The silylperoxides are convertible into enantioenriched chiral acyloins in a stereospecific manner.

DOI： 10.1002/chem.201402996

Repository Public URL： https://hdl.handle.net/2324/7172101

Language：English   Publishing type：Research paper (scientific journal)  

Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

DOI： 10.1021/ja209553f

Repository Public URL： https://hdl.handle.net/2324/7172100

Language：English   Publishing type：Research paper (scientific journal)  

Acyloins are efficiently synthesized in three steps from alkynes via hydrosilylation followed by an addition-type ozone oxidation and hydrogenation. The key intermediate alpha-silylper-oxy ketone is convertible to not only acyloin but also O-silylated acyloin and diketone.

DOI： 10.1246/cl.2011.233

Repository Public URL： https://hdl.handle.net/2324/7172099

Event date： 2025.3

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Venue：福岡   Country：Japan  

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Venue：online   Country：Japan  

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