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

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

ISSN (print)

00223263

ISSN (electronic)

15206904

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