Synthesis of Enantiopure C3-Symmetric Triangular Molecules

Tomoya Miura; Takayuki Nakamuro; Scott G. Stewart; Yuuya Nagata; Masahiro Murakami

doi:10.1002/anie.201612585

Synthesis of Enantiopure C₃-Symmetric Triangular Molecules

Tomoya Miura, Takayuki Nakamuro, Scott G. Stewart, Yuuya Nagata, Masahiro Murakami

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

An asymmetric synthesis of C₃-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C₃-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.

Original language	English
Pages (from-to)	3334-3338
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	12
DOIs	https://doi.org/10.1002/anie.201612585
Publication status	Published - 13 Mar 2017

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abstract = "An asymmetric synthesis of C3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C3-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.",

keywords = "Asymmetric synthesis, C-symmetry, Cyclotrimerization, Macrocycles, Rhodium",

author = "Tomoya Miura and Takayuki Nakamuro and Stewart, {Scott G.} and Yuuya Nagata and Masahiro Murakami",

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T1 - Synthesis of Enantiopure C3-Symmetric Triangular Molecules

AU - Miura, Tomoya

AU - Nakamuro, Takayuki

AU - Stewart, Scott G.

AU - Nagata, Yuuya

AU - Murakami, Masahiro

PY - 2017/3/13

Y1 - 2017/3/13

N2 - An asymmetric synthesis of C3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C3-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.

AB - An asymmetric synthesis of C3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C3-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.

KW - Asymmetric synthesis

KW - C-symmetry

KW - Cyclotrimerization

KW - Macrocycles

KW - Rhodium

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U2 - 10.1002/anie.201612585

DO - 10.1002/anie.201612585

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Synthesis of Enantiopure C₃-Symmetric Triangular Molecules

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