Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation

Shveta Pandiancherri, David W Lupton

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Abstract

Exposure of N-chloroamines to (KOBu)-Bu-t or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of pi 4s + pi 2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. (C) 2010 Published by Elsevier Ltd.
Original languageEnglish
Pages (from-to)671 - 674
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number6
DOIs
Publication statusPublished - 2011

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