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Synfacts 2013; 9(12): 1355
DOI: 10.1055/s-0033-1340237
DOI: 10.1055/s-0033-1340237
Polymer-Supported Synthesis
Asymmetric Ring-Opening of meso-Epoxides with a Chiral Metal-Organic Framework
Regati S, He Y, Thimmaiah M, Li P, Xiang S, Chen B, * Zhao JC.-G. * University of Texas at San Antonio, USA and Fujian Normal University, Fuzhou, P. R. of China
Enantioselective Ring-Opening of meso-Epoxides by Aromatic Amines Catalyzed by a Homochiral Metal-Organic Framework.
Chem. Commun. 2013;
49: 9836-9838
Enantioselective Ring-Opening of meso-Epoxides by Aromatic Amines Catalyzed by a Homochiral Metal-Organic Framework.
Chem. Commun. 2013;
49: 9836-9838
Further Information
Publication History
Publication Date:
18 November 2013 (online)
Significance
A chiral MOF (UTSA-32) was prepared from (S)-4,4′-dibromo-6,6′-dichloro-2,2′-diethoxy-1,1′-binaphthyl in three steps (eq. 1). UTSA-32 catalyzed the enantioselective ring opening of meso-epoxides with anilines to give the corresponding α-hydroxyamines in 69–95% yield with 12–89% ee (11 examples, eq. 2).
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Comment
UTSA-32 was characterized by single-crystal X-ray diffraction, PXRD, TGA, and BET analyses. Single-crystal X-ray diffraction analysis of UTSA-32 revealed that the binuclear zinc clusters are bridged by the carboxylic groups of organic linker L to form a three-dimensional framework.
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