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Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and Its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts
Author(s) -
Shirakawa Seiji,
Shimizu Shoichi
Publication year - 2009
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.200801288
Subject(s) - moiety , chemistry , diastereomer , enantioselective synthesis , amino acid , chirality (physics) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The synthesis of an inherently chiral calix[4]arene amino acid as a chiral building block has been achieved in order for subsequent transformation to various types of inherently chiral calix[4]arenes. The optically pure, inherently chiral calix[4]arene amino acids were prepared by the separation of a diastereomeric mixture of calix[4]arene amino acid derivatives bearing a ( R )‐BINOL moiety. The separated optically pure calix[4]arene amino acid derivatives with a ( R )‐BINOL moiety were easily transformed to novel inherently chiral calix[4]arenes containing an amino alcohol structure or a quaternary ammonium moiety. These optically pure chiral calix[4]arenes were applied to asymmetric reactions as organocatalysts.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)