Synthesis of Enantiopure C-3-Symmetric Triangular Molecules

An asymmetric synthesis of C-3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C-3-symmetric triangular macrocycle motif. This method can be applied to the synthesis of an...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 12; pp. 3334 - 3338
Main Authors Miura, Tomoya, Nakamuro, Takayuki, Stewart, Scott G., Nagata, Yuuya, Murakami, Masahiro
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.03.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
CHIRAL RECOGNITION
POLYPHENYLENES
C-3-symmetry
C-3 SYMMETRY
RESOLUTION
1-SULFONYL-1,2,3-TRIAZOLES
ALKYNE
MACROCYCLIC HOSTS
SATURATED HETEROCYCLES
asymmetric synthesis
cyclotrimerization
macrocycles
TRIBENZOTRIQUINACENE
rhodium
C3-symmetry
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Summary:An asymmetric synthesis of C-3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C-3-symmetric triangular macrocycle motif. This method can be applied to the synthesis of an enantiopure hydrocarbon, which owes its chirality to asymmetric distribution of H/D atoms on the benzene rings.
Bibliography:KAKEN
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201612585