Citation: Jue Xiao CAI, Zheng Hong ZHOU, Kang Ying LI, Chi Hung YEUNG, Chu Chi TANG. A New Convenient Method for the Resolution of 1,1'-Binaphthalene-2,2'-diol Via a Phosphite Using (-)-Menthol as Resolving Agent[J]. Chinese Chemical Letters, ;2002, 13(7): 617-619. shu

A New Convenient Method for the Resolution of 1,1'-Binaphthalene-2,2'-diol Via a Phosphite Using (-)-Menthol as Resolving Agent

1.
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071;
2.
Open Laboratory of Chirotechnology and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong

Received Date: 26 April 2001
Revised Date: 16 January 2002

Fund Project: Financial Support by the National Natural Science Foundation of China (No.29872016) and the Hong Kong Polytechnic University ASD Fund are gratefully acknowledged.

(-)-Menthol reacts with phosphorus trichloride to afford menthyl phosphorodichloridite 2,which further reacts with racemic 1, 1'-binaphthalene-2, 2'-diol to give phosphite (±)-3 in the presence of triethylamine. (±)-3 can be easily separated by fractional crystallization to form the crystal (+)-(S)-3 and the mother liquor (-)-(R)-3. Then both the crystal and the mother liquor are treated with AcOH-H₂0 to obtain enantiomeric pure (-)-(S)-1 and (+)-(R)-1 respectively, with enantiomeric excess up to 99.7%.
- optically active 1,l'-binaphthalene-2,2'-diol,
- L-menthol,
- phosphite,
- fractional crystal lization,
- resolution
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