Efficient Thia‐Bridged Triarylamine Heterohelicenes: Synthesis, Resolution, and Absolute Configuration Determination

Abstract

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2008/z800705_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.