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Synthesis of Enantiopure C 3 ‐Symmetric Triangular Molecules
Author(s) -
Miura Tomoya,
Nakamuro Takayuki,
Stewart Scott G.,
Nagata Yuuya,
Murakami Masahiro
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201612585
Subject(s) - enantiopure drug , chirality (physics) , chemistry , rhodium , molecule , benzene , enantioselective synthesis , stereochemistry , catalysis , organic chemistry , physics , chiral symmetry , quantum mechanics , quark , nambu–jona lasinio model
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.