%0 Journal Article
%A Pearson, William H.
%A Mans, Douglas M.
%A Kampf, Jeff W.
%D 2004
%T Cycloadditions of 2-Azaallyllithium Species with Conjugated
Polyenes
%U https://acs.figshare.com/articles/journal_contribution/Cycloadditions_of_2_Azaallyllithium_Species_with_Conjugated_Polyenes/3349156
%R 10.1021/jo030306z.s001
%2 https://acs.figshare.com/ndownloader/files/5188468
%K R 2
%K azaallyllithium
%K novel bridged azabicyclic compounds
%K cyclic dienes
%K species
%K azabicyclo
%K R 1
%K CH
%K diastereoselective endo fashion
%K Azaallyllithium
%X 2-Azaallyllithium species [R1CH(−)NC(X)R2Li(+), where R1 and R2 are alkyl and X = OMe] were
generated by tin−lithium exchange of (2-azaallyl)stannanes and underwent [π4s+π2s] and
[π6s+π4s] cycloadditions with cyclic dienes and trienes, respectively, to generate novel bridged
azabicyclic compounds in a highly diastereoselective endo fashion. The periselectivity using
cycloheptatriene was modest, producing a 1:1 mixture of [π6s+π4s] and [π4s+π2s] adducts. The
reactions of 2-azaallyllithium species with dienes proceeded by a [π4s+π2s] pathway. The
cycloadducts derived from cyclic 2-azaallyllithium species possess the 7-azabicyclo[2.2.1]heptane
(tropane) or 8-azabicyclo[3.2.1]octane ring system and have been elaborated into cocaine-like
analogues.
%I ACS Publications