Tetrabutylammonium Fluoride → HCID 22345111, compound

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Reaction Steps

An optically active binaphthol (VII) is reacted with bromine in acetic anhydride to obtain 6,6′-dibromo-2,2′-dihydroxy-1,1′-binaphthyl (XII). The hydroxyl groups of compound (XII) are protected using tert-butyldimethylsilyl oxytriflate (TBDMSOTf) and 2,6-lutidine to obtain 6,6′-dibromo-2,2′-bis(tert-butyldimethylsilyloxy)-1,1′-binaphthyl (XIII). Compound (XIII) is converted to an anion form using sec-butyllithium (sec-BuLi), and dimethylformamide (DMF) is caused to act thereon to obtain 6,6′-diformyl-2,2′-bis(tert-butyldimethylsilyloxy)-1,1′-binaphthyl (XIV). Compound (XIV) is reacted with triphenylmethylphosphonium bromide (Ph3P+CH3Br−) and potassium t-butoxide (t-BuOK) to obtain 6,6′-divinyl-2,2′-bis(tert-butyldimethylsilyloxy)-1,1′-binaphthyl (XV). Compound (XV) is reacted with tetrabutylammonium fluoride (TBAF) for silyl removal to obtain 6,6′-divinyl-2,2′-dihydroxy-1,1′-binaphthyl, which is heated together with phosphorus trichloride to obtain 6,6′-divinyl-1,1′-binaphthalene-2,2′-dioxychlorophosphine (XVI). The 6,6′-divinyl-1,1′-binaphthalene-2,2′-dioxychlorophosphine (XVI) is reacted with 2′-diphenylphosphino-2-hydroxy-1,1′-binaphthyl (XI) in the presence of triethylamine (NEt3) to obtain 2′-diphenylphosphino-1,1′-binaphthalen-2-yloxy(6,6′-divinyl-1,1′-binaphthalene-2,2′-diyloxy)phosphine (XVII).

Provenance & Evidence