Resolution and some properties of (1,1')-bi(dibenzofuranyl)-2,2'-diol (BIFOL)

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作者
Gelpke, AES [1 ]
Fraanje, J [1 ]
Goubitz, K [1 ]
Schenk, H [1 ]
Hiemstra, H [1 ]
机构
[1] UNIV AMSTERDAM,AMSTERDAM INST MOL STUDIES,ORGAN CHEM LAB,NL-1018 WS AMSTERDAM,NETHERLANDS
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The resolution of C-2-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 phosphoramidates. It is shown that the bidibenzofuran skeleton undergoes sulfonation reactions with high regioselectivity. (C) 1997 Elsevier Science Ltd.
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页码:5899 / 5908
页数:10
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