Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active β-amino alcohols via 1-oxy-substituted alkyllithium …

J Schwerdtfeger, S Kolczewski, B Weber, R Fröhlich…

Index: Schwerdtfeger, Joerg; Kolczewski, Sabine; Weber, Berthold; Froehlich, Roland; Hoppe, Dieter Synthesis, 1999 , # 9 p. 1573 - 1592

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Citation Number: 24

Abstract

Abstract: A facile protocol for the electrophilic C-substitution (methylation, acylation, a- hydroxyalkylation, and carboxylation) of several 2-(N, N-dibenzylamino) alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection between the diastereotopic a-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S- ...

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