Tetrahedron p. 5899 - 5908 (1997)
Update date:2022-08-05
Topics:
Gelpke, Arjan E. Sollewijn
Fraanje, Jan
Goubitz, Kees
Schenk, Henk
Hiemstra, Henk
The resolution of C2-symmetric (1,1')-bi(dibenzofuranyl)-2,2'-diol (BIFOL) is reported. Separation via recrystallisation of its 1:1 mixture of diastereomeric cyclic phosphoramidates by using (-)-(S)-1-phenylethylamine as chiral auxiliary gave both enantiomers in >98% enantiopurity and in good chemical yields. The configuration of BIFOL was determined by X-ray analysis of one of the diastereomeric phosphoramides. It is shown that the bidibenzofuran skeleton undergoes sulfonation reactions with high regioselectivity.
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