Design of a novel inherently chiral calix[4]arene for chiral molecular recognition

Seiji Shirakawa; Akihiro Moriyama; Shoichi Shimizu

doi:10.1021/ol071249p

Design of a novel inherently chiral calix[4]arene for chiral molecular recognition

Org Lett. 2007 Aug 2;9(16):3117-9. doi: 10.1021/ol071249p. Epub 2007 Jul 6.

Authors

Seiji Shirakawa¹, Akihiro Moriyama, Shoichi Shimizu

Affiliation

¹ Department of Applied Molecular Chemistry and High Technology Research Center, College of Industrial Technology, Nihon University, Narashino, Chiba, 275-8575, Japan.

PMID: 17616144
DOI: 10.1021/ol071249p

Abstract

A newly designed inherently chiral calix[4]arene was synthesized and resolved to an optically pure form. Enantiomeric recognition ability of the chiral calix[4]arene was examined using 1H NMR experiments with mandelic acid. In addition, the chiral calix[4]arene was applied to asymmetric reactions, as an organocatalyst.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Calixarenes / chemical synthesis*
Calixarenes / chemistry
Catalysis
Magnetic Resonance Spectroscopy
Mandelic Acids / chemistry
Molecular Structure
Phenols / chemical synthesis*
Phenols / chemistry
Stereoisomerism

Substances

Mandelic Acids
Phenols
calix(4)arene
Calixarenes
mandelic acid