Premium
A Novel C 3 ‐Symmetric Triol as Chiral Receptor for Ammonium Ions
Author(s) -
Fabris Fabrizio,
Pellizzaro Leonardo,
Zonta Cristiano,
De Lucchi Ottorino
Publication year - 2007
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.200600673
Subject(s) - chemistry , enantiopure drug , enantiomer , camphor , ammonium , potassium , hydrazone , ion , triol , medicinal chemistry , halogenation , chloride , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , diol , catalysis
The enantiopure C 3 ‐symmetric syn ‐benzotriborneol was efficiently obtained in an eight‐step route. Of particular interest from a synthetic point of view are the potassium tert ‐butoxide promoted bromination of camphor hydrazone ( 4 ) and the observation that the protecting groups influence the syn / anti diasteroselectivity of the cyclotrimerization reaction of 12 – 14 . Complexation studies in deuteriochloroform revealed the capability of the cyclotrimer syn ‐ 1 to act as host for ammonium ions, and in particular, the efficient chiral recognition of the two enantiomers of (1‐phenylethyl)ammonium chloride. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)