Synthesis, Optical Resolution and Enantiomeric Recognition Ability of Novel, Inherently Chiral Calix[4]arenes: Trial Application to Asymmetric Reactions as Organocatalysts | Zendy

Shirakawa Seiji | Zendy; Moriyama Akihiro | Zendy; Shimizu Shoichi | Zendy

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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

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)

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