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Chiral calixarenes derived from resorcinol
Author(s) -
Iwanek Waldemar,
Mattay Jochen
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508199
Subject(s) - chemistry , enantiomer , resorcinol , moiety , chirality (physics) , calixarene , recrystallization (geology) , stereochemistry , mannich reaction , enantioselective synthesis , ring (chemistry) , combinatorial chemistry , organic chemistry , molecule , catalysis , paleontology , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , biology , quark
A new type of chiral resorc[4]arene is described. The formation of both enantiomers of 5 is controlled by the chirality of the amines used in the Mannich reaction leading to the 1,3‐oxazine ring anellated to the resorcarene moiety. At −50°C ee increases up to 90%. Both enantiomers can be easily purified to >98% ee by recrystallization. The structures were proved by standard methods including X‐ray analysis.
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