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A New and Practical Method for Preparing Enantiomerically Pure [1,1′‐Binaphthalene]‐2,2′‐diol: Resolution of Racemic [1,1′‐Binaphthalene]‐2,2′‐diol with threo ‐(1 S ,2 S )‐2‐Amino‐1‐(4‐nitrophenyl)propane‐1,3‐diolCyclohexanone Condensate
Author(s) -
Liu Dejun,
Shan Zixing,
Liu Fei,
Xiao Chunguang,
Lu Guojian,
Qin Jingui
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390006
Subject(s) - chemistry , diol , boric acid , cyclohexanone , yield (engineering) , derivative (finance) , organic chemistry , medicinal chemistry , catalysis , materials science , economics , financial economics , metallurgy
An economic and practical method for preparing enantiomerically pure [1,1′‐binaphthalene]‐2,2′‐diols is reported. Thus, a condensate of threo ‐(1 S ,2 S )‐2‐amino‐1‐(4‐nitrophenyl)propane‐1,3‐diol and cyclohexanone (CHANP) was used as a resolving agent. A 2 : 1 : 1 mixture of racemic [1,1′‐binaphthalene]‐2,2′‐diol, boric acid, and CHANP was refluxed for several hours in THF or MeCN to give a white precipitate of bis{( R )‐[1,1′‐binaphthalene]‐2,2′‐diol}boric acid CHANP derivative, from the precipitate, and a filtrate separated from the precipitate, ( R )‐ and ( S )‐[1,1′‐binaphthalene]‐2,2′‐diol of 100% ee were obtained in ca. 65% yield, respectively.