Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-Tetrahydroxytetraphenylenes

Language

English

Abstract

Asymmetric synthesis of (R,R)- and (S,S)-1,8,9,16- tetrahydroxytetraphenylenes was achieved from starting material (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol respectively by utilizing a center-to-axis strategy. A series of crown ether compounds 20, 24, and 25 and their corresponding enantiomers derived from chiral tetrahydroxytetraphenylene were synthesized in enantiomerically pure forms. Enantiomeric recognition properties of these hosts toward l- and d-amino acid methyl ester hydrochloride were studied by the UV spectroscopy titration. The tetramer hosts (S,S,S,S,S,S,S,S)-20 and (R,R,R,R,R,R,R,R)-20 exhibited the best enantioselectivities toward l- and d-alanine methyl ester hydrochloride salt with KL/KD = 4.1 and KD/KL = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host-guest chemistry. © 2013 American Chemical Society.

Publication Date

2013

Source Publication Title

Journal of Organic Chemistry

Volume

78

Issue

17

Start Page

8562

End Page

8573

Publisher

American Chemical Society

DOI

10.1021/jo401240k

Link to Publisher's Edition

http://dx.doi.org/10.1021/jo401240k

ISSN (print)

00223263

ISSN (electronic)

15206904

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