An efficient preparation of optically pure C2-symmetric aromatic diols by the asymmetric reduction of diacylaromatic compounds with B-chlorodiisopinocampheylborane

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3795-3798

  Ramachandran, P Veeraraghavan ^a   Chen, Guang Ming ^a   Lu, Zhi Hui ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; REDUCTION;

EID: 0029888342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00708-3     Document Type: Article

References (24)

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16. 21 we isolated only the enantiomerically pure diol.
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21. Ramachandran, P. V.; Chen, G. M.; Brown, H. C. Manuscript ready for publication.
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24. 13C NMR. In the case of the acetylpyridines 2e and 2f, once the reaction was complete, 3N dilute HCl (3 equiv) was added to the reaction mixture and stirred for 30 min. The organic layer was removed by extracting with EE and the aqueous layer was treated with aqueous 3N NaOH to pH 9. The product was extracted with ethyl acetate after saturating the aqueous layer with sodium chloride. The crude product was further purified by chromatography over silica.