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-(1S,2S)-2-Amino-1-(4-nitrophenyl)propane-1,3-diolCyclohexanone Condensate

✍ Scribed by Dejun Liu; Zixing Shan; Fei Liu; Chunguang Xiao; Guojian Lu; Jingui Qin

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 80 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390006

✦ Synopsis

Abstract

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.