In summary we have shown a very practical access to thia-bridged triarylamine hetero[4]- and -[6]helicenes by four consecutive (one-pot) electrophilic regioselective aromatic sulfur insertions. Owing to their remarkably high racemization barrier, these derivatives can be resolved by HPLC, and the absolute configuration for 7a has been determined as P-(+) by ab initio calculations and by experimental measurement of VCD spectra.
Efficient Thiabridged Triarylamine Heterohelicenes Synthesis, Resolution and Absolute Configuration Determination / G. Lamanna; C. Faggi; F. Gasparrini; A. Ciogli; C. Villani; J. P. Stephens; J. F. Devlin; S. Menichetti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 14:(2008), pp. 5747-5750. [10.1002/chem.200800705]
Efficient Thiabridged Triarylamine Heterohelicenes Synthesis, Resolution and Absolute Configuration Determination
FAGGI, CRISTINA;MENICHETTI, STEFANO
2008
Abstract
In summary we have shown a very practical access to thia-bridged triarylamine hetero[4]- and -[6]helicenes by four consecutive (one-pot) electrophilic regioselective aromatic sulfur insertions. Owing to their remarkably high racemization barrier, these derivatives can be resolved by HPLC, and the absolute configuration for 7a has been determined as P-(+) by ab initio calculations and by experimental measurement of VCD spectra.
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