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A Configurationally Stable Chiral Concave Imidazolinium Salt
Author(s) -
Reimers Tim,
Näther Christian,
Lüning Ulrich
Publication year - 2011
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.201001367
Subject(s) - chemistry , metathesis , salt (chemistry) , carbene , aniline , reagent , ring (chemistry) , salt metathesis reaction , crystal structure , crystallography , stereochemistry , polymer chemistry , organic chemistry , catalysis , polymerization , polymer
Abstract Starting from symmetric bis‐ ortho ‐alkenyl‐substituted aniline 11 and unsymmetric bis‐alkenyl‐substituted aminonaphthalene 12 , imidazolinium salt 17 has been prepared. Salt 17 was cyclized by ring‐closing metathesis, and hydrogenation gave axially chiral N‐heterocyclic carbene precursor 19 . The configurational stability of 19 was proven by temperature‐dependent NMR studies and also by the use of Λ‐BINPHAT as a chiral shift reagent. Compound 19 was also characterized by single‐crystal X‐ray diffraction.