Nonracemic Menthyl Phosphorylacetates

Abstract

Terpenes U 0200 Nonracemic Menthyl Phosphorylacetates -[synthesis and structure characterization; 6 examples]. -(BREDIKHIN*, A. A.; ELISEENKOVA, R. M.; TARASOVA, R. I.; VOSKRESENSKAYA, O. V.; BALANDINA, A. A.; DOBRYNIN, A. B.; LATYPOV, S. K.; LITVINOV, I. A.; SHARAFUTDINOVA, D. R.; EFREMOV, Y. Y.; Russ.

Crystallographic evidence of side-arm lariat effect in the series of chiral ortho- and para-methoxyphenoxymethyl-15-crown-5 complexes with sodium perchlorate

“…Mp 79-81°C (n-hexane/benzene) ½a 20 D ¼ þ7:5 (c 0.6, EtOH); 95% ee [7]. The syntheses of (S)-[(2-methoxyphenoxy)methyl]-15-crown-5 [(S)-2, pale yellow oil; ½a 20 D ¼ À13:1 (c 1.1, CHCl 3 ); 99.1% ee] and (S)-[(4-methoxyphenoxy)methyl]-15-crown-5 [(S)-3, pale yellow oil; ½a 20 D ¼ À13:8 (c 6.9, CHCl 3 ); 92.0% ee] from the corresponding diols and tetraethyleneglycol di(p-toluenesulfonate) 7 were described in detail earlier [7]. Racemic crowns 2 and 3 as yellowish oils were prepared by analogy from rac-(2-methoxyphenoxy)propane-1,2-diol and rac-(4-methoxyphenoxy)propane-1,2-diol, correspondingly.…”

“…Enantiopure compound 4 was used by us as the key precursor for the family of nonracemic crowns. The binding and chiral recognition ability of the so obtained hosts with respect to some chiral ammonium salts in solutions was investigated and discussed [7]. The advantages of crown 2 over crown 3 have been also demonstrated there.…”