Preparation of enantiomerically pure 1,1'-bi-2-naphthol via cyclic borate ester

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2847-2850

  Shan, Zixing ^a   Wang, Guoping ^a   Duan, Biao ^a   Zhao, Dejie ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; NAPHTHOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030271755     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00375-8     Document Type: Article

References (32)

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32. 8. For example, the solid obtained from reacting of 1.1′ - bi - 2 - naphthol with an excess of boric acid or trimethoxyborane in boiling toluene or benzene (using 4A molecular sieve or anhydrous zinc chloride etc. as methanol - absorbing meterial), reacted with quinine under refluxing condition in the same solvents as above for 3 - 5h to produce a white precipitate of 1 . 1′ - bi - 2 - naphtholborane quinine derivative and a mother liquor. The mother liquor and the precipitate were treated in accordance with the procedure in the Experimental of the paper, (R) - (+) - and (S) - (-) - 1.1′ - bi - 2 - naphthol were obtained with 54 - 78% yield and 92 - 100%ee. Study on the optimum conditions for the resolution of 1.1′ - bi - 2 - naphthol using trimethoxyborane or boric acid as borate source is proceeding.