B. Bertini, M. Perrin, D. Sinou
Dec 31, 2003
Citations
0
Influential Citations
8
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
Reaction of pseudo‐glucal 1 with Grignard reagents derived from 1‐bromo‐4‐(trimethylsilyloxy)benzene, 1‐bromo‐4‐methoxybenzene, 1‐bromo‐4‐methoxymethoxybenzene, 1‐bromo‐4‐dimethylaminobenzene, in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated β‐C‐aryl glycosides 2. Desilylation and hydrogenation of 2 leads to β‐C‐aryl glycosides 4, which can be used as chiral precursor compounds in the synthesis of chiral liquid crystals. Combination of 4 with arylaldehydes leads to compounds 5–7, whereas reaction with p‐alkoxysubstituted phenylboronic acids gives the trioxaboradecalins 8–11. The mesogenic properties of these compounds are strongly influenced by the nature of the substituent on the phenyl ring in the molecule. †This paper is dedicated to Professor Gérard Descotes on the occasion of his 70th birthday.