Synthesis p. 176 - 182 (1997)
Update date:2022-07-30
Topics:
Boie, Christiane
Hoppe, Dieter
2-[N-(Diphenylmethyleneamino)]alkyl carbamates are deprotonated by means of sec-butyllithium in the presence of TMEDA or (-)-sparteine and the diastereomeric ion pairs of α-oxycarbanions formed are substituted by severa1 electrophiles. Deprotection proceeds smoothly to yield chain-elongated β-amino alcohols. Problems arise due to nucleophilic attack of the alkyllithium at one aryl ring of the benzophenone imines under certain reaction conditions.
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