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Reductive cleavage of axially disymmetric tertiary amines and quaternary ammonium salts by lithium aluminium hydride. Synthesis of new 1,1′-binaphthyl substituted amines

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
26
Issue
4
Identifiers
DOI: 10.1016/s0040-4039(00)61900-7

Abstract

Abstract Axially disymmetric tertiary amines or quaternary ammonium salts A are synthesized by double alkylation of primary or secondary amines with racemic or optically pure 2,2′-bis (bromomethyl)-1,1′-binaphthyl. Their reductive cleavage by lithium aluminium hydride in refluxing THF leads to chiral secondary or tertiary amines B , substituted by a binaphthyl unit, with high yields and absence of racemization.

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