55611-45-5Relevant academic research and scientific papers
DIRECT REGIO- AND STEREO-SELECTIVE LITHIATION OF SECONDARY ALLYL AND METHYLALLYL AMINES: A NEW TYPE OF γ-AMINATED ORGANOLITHIUM REAGENTS IN ORGANIC SYNTHESIS
Barluenga, Jose,Foubelo, Francisco,Fananas, Francisco J.,Yus, Miguel
, p. 1524 - 1552 (2007/10/02)
Several secondary allyl and methylallylamines (6) have been regio- and stereo-selectively lithiated with t-butyl-lithium, giving the corresponding sp2 γ-aminated organolithium intermediates (7), which by reaction with electrophiles D2O, Me2S2,
Synthesis of Secondary Allylic Amines
Kimpe, Norbert de,Stanoeva, Elena,Verhe, Roland,Schamp, Niceas
, p. 587 - 592 (2007/10/02)
Secondary allylic amines were synthesized from aldehydes and primary amines via successive conversion into aldimines, α-haloaldimines and α,β-unsaturated aldimines, the latter being selectively reduced by sodium borohydride at the imino function.This method allowed the synthesis of secondary allylic amines with high preponderance of the E-stereochemistry.A comparison was made with an alternative method involving the generation of α,β-unsaturated aldimines from α,β-unsaturated aldehydes and primary amines, and subsequent borohydride reduction.
