Synthesis of Novel Enantiomers Cyclophanes Using 2,2'-Diethynyl-1,1'-binaphthyls as a Structural Block and Their Optical Properties

Abstract

Abstract: We employed (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with a highly stable chirality as the structural blocks and investigated the synthesis of two topologically interesting tetrabinaphthyl cage compounds (R,R,R,R)-2 and (S,S,S,S)-2 via the multi steps reactions including the introduction of protecting group, linking of benzene-bridge, removal of protecting group as well as intermolecular cross-coupling. As expected, the results from MS, IR, UV-Vis, ¹H, ¹³CNMR, elemental analysis and optical properties indicate that this method is very effective for obtaining compound 2 in enantiomer form. The enantiomer relation of the two isomers was reflected unambiguously by their circular dichroism(CD) spectra with exact mirror images and specific rotations [α]_D data.

Key words: Optical activity, Binaphthyl derivatives, Structural block, Cyclophane compound, Enantiomer

CLC Number:

O624

TrendMD:

AN De-Lie, YANG Shao-Hui, ZHANG Zhi-Yang, PENG Zhi-Hong, ZHANG Ying-Jun, LIU Hong-Ling. Synthesis of Novel Enantiomers Cyclophanes Using 2,2'-Diethynyl-1,1'-binaphthyls as a Structural Block and Their Optical Properties[J]. Chem. J. Chinese Universities, 2005, 26(7): 1268.

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Synthesis of Novel Enantiomers Cyclophanes Using 2,2'-Diethynyl-1,1'-binaphthyls as a Structural Block and Their Optical Properties

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