Stereoselective Synthesis of Enantipure β-Amino Alcohols via Nucleophilic β-Amino-α-hydroxyalkylation by Means of 1-Lithiated 2-[N-(Diphenylmethyleneamino)]alkyl Carbamates

Christiane Boie; Dieter Hoppe

doi:10.1055/s-1997-1155

Synthesis 1997; 1997(2): 176-182
DOI: 10.1055/s-1997-1155

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Stereoselective Synthesis of Enantipure β-Amino Alcohols via Nucleophilic β-Amino-α-hydroxyalkylation by Means of 1-Lithiated 2-[N-(Diphenylmethyleneamino)]alkyl Carbamates

Christiane Boie, Dieter Hoppe^*

^*Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany, Fax +49(251)8339772

Abstract

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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 several 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.

1-lithioalkyl carbamates - β-amino alkanols - imines - deprotonation

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