Premium
Efficient Thia‐Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination
Author(s) -
Lamanna Giuseppe,
Faggi Cristina,
Gasparrini Francesco,
Ciogli Alessia,
Villani Claudio,
Stephens Philip J.,
Devlin Frank J.,
Menichetti Stefano
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800705
Subject(s) - absolute configuration , electrophile , circular dichroism , chemistry , ab initio , spectral line , resolution (logic) , helicity , computational chemistry , crystallography , stereochemistry , physics , computer science , organic chemistry , particle physics , quantum mechanics , catalysis , artificial intelligence
One, two, three, four: twist! Four consecutive (one‐pot) electrophilic sulfur insertions on triarylamines with phthalimidesulfenyl chloride (see scheme), offer an easy access to chiral hetero[4]‐ and ‐[6]helicenes that are remarkably stable against a reversal of the helicity. These heterohelicenes were resolved by HPLC on an amylose‐based chiral stationary phase, and the absolute configuration was established by ab initio calculations and experimental vibrational circular dichroism spectra.