par Ben Hassine, Béchir;Gorsane, Mohamed 
;Evrard, France ;Pecher, Jacques ;Martin, Ricardo;Castelet, Daniel
Référence Bulletin des Sociétés chimiques belges, 95, 7, page (547-556)
Publication Publié, 1986
;Evrard, France ;Pecher, Jacques ;Martin, Ricardo;Castelet, DanielRéférence Bulletin des Sociétés chimiques belges, 95, 7, page (547-556)
Publication Publié, 1986
Article révisé par les pairs
| Résumé : | Atrolactic syntheses have been carried out to evaluate the potentiality, in asymmetric syntheses, of chiral inducers. The (dl)‐hydroxyhelicenes 1, 2, the (dl) sec. alcohols 3–12 and the (dl) phenolic binaphtyl compound 15 have been used as inducers. The d.e. are collected in table I (6–100%). The atrolactic asymmetric synthesis has also been carried out using three optically active inducers, namely: (‐)‐quinine 13, (‐)‐10, 11‐dihydroquinine 14, and R(‐)‐2, 2, 2‐trifluoro‐1‐(9‐anthryl) ethanol 6. Diastereomeric and enantiomeric excesses equal or greater than 88% have been obtained in six cases out of sixteen: (dl)‐2‐hydroxyheptahelicene 1 (d.e=100%±2), (1‐naphtyl)‐(9‐anthryl) methanol 3 (d.e=90%); 2, 2, 2‐trichloro‐1‐(9‐anthryl) ethanol 7 (d.e=100%±2), 2, 2, 2‐tribromo‐1‐(9‐anthryl) ethanol 8 (d.e=100%±2), (‐)‐quinine 13 (e.e=95.5%), and (‐)‐2, 2, 2‐trifluoro‐1‐(9‐anthryl) ethanol 6 (e.e=88%). Copyright © 1986 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
