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Synthesis, Optical Resolution and Enantiomeric Recognition Ability of Novel, Inherently Chiral Calix[4]arenes: Trial Application to Asymmetric Reactions as Organocatalysts
Author(s) -
Shirakawa Seiji,
Moriyama Akihiro,
Shimizu Shoichi
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800850
Subject(s) - mandelic acid , chemistry , enantiomer , enantiomeric excess , enantioselective synthesis , phenol , chiral resolution , catalysis , chiral derivatizing agent , resolution (logic) , combinatorial chemistry , organocatalysis , nuclear magnetic resonance spectroscopy , organic chemistry , chiral column chromatography , artificial intelligence , computer science
Abstract Newly designed, inherently chiral calix[4]arenes containing amino phenol structures have been synthesized and resolved to optically pure forms. The enantiomeric recognition ability of one chiral calix[4]arene was examined with mandelic acid by 1 H NMR spectroscopy, and we found that the inherently chiral calix[4]arene could be used as a chiral NMR solvating agent to determine the enantiopurity of mandelic acid at ambient temperature. In addition, the chiral calix[4]arenes were used as organocatalysts in asymmetric Michael‐type addition reactions of thiophenols, and high catalytic efficiency with low enantioselectivity was observed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)