313048-26-9Relevant academic research and scientific papers
Preparation of planar chiral amino phenols based on the [2.2]paracyclophane backbone
Dahmen, Stefan,Braese, Stefan
, p. 2845 - 2850 (2001)
The synthesis of various planar and central chiral secondary and tertiary amino phenols based on the [2.2]paracyclophane backbone is described. Planar chiral tertiary amino phenols are prepared by reductive amination of 5-formyl-4-hydroxy[2.2]paracyclopha
Regioselective fries rearrangement and friedel-crafts acylation as efficient routes to novel enantiomerically enriched ortho-acylhydroxy[2.2]paracyclophanes
Rozenberg, Valeria,Danilova, Tat'yana,Sergeeva, Elena,Vorontsov, Evgenii,Starikova, Zoya,Lysenko, Konstantin,Belokon', Yuri
, p. 3295 - 3303 (2007/10/03)
Two useful approaches to ortho-acylhydroxy[2.2]paracyclophanes, starting from 4-hydroxy[2.2]paracyclophane, have been developed. TiCl4-catalyzed Fries rearrangement and direct acylation occur regioselectively (to the ortho position with respect to the hydroxy group), leading to 4-acetyl-5-hydroxy[2.2]paracyclophane (3) and 4-benzoyl-5-hydroxy[2.2]-paracyclophane (4) in high to excellent chemical yields. For compound 4, an X-ray investigation has been performed. ortho-Acylhydroxy[2.2]paracyclophanes 3 and 4 have been obtained in enantiomerically enriched forms (ee 92-99%) and the absolute configurations of their enantiomers have been determined.
