75059-00-6Relevant articles and documents
Aminosilanes in organic synthesis. Hydrostannation of N,N-bis(trimethylsilyl)propargylamine. Facile and selective routes to (E)-allylic amines
Corriu, R.J.P.,Bolin, G.,Moreau, J.J.E.
, p. 273 - 280 (2007/10/02)
The addition of tributyl tin hydride to N,N-bis(trimethylsilyl)propargylamine yielded E-1-tributylstannyl-3-prop-1-ene 2 in 90percent yield and 96percent stereochemical purity.The functional vinyl tin reagent 2 was shown to give short and selective access to primary allylic amines.The reactions of 2 with aryl and vinyl bromides in the presence of a palladium catalyst gave substituted E-allylic amines in high yields.The reaction of 2 with butyl lithium yielded E-γ-vinyl lithium from which selective access to E-allylic amines was obtained.Key words: silylamines / propargylamines / hydrostannation / vinyl tin / vinyl lithium / (E)-allylamines
A simple synthesis of primary E-allylic amines from 1-tributylstannyl-3-bis(trimethylsilyl)amino prop-1-ene
Corriu,Bolin,Moreau
, p. 4121 - 4124 (2007/10/02)
A facile and selective preparation of primary E-allylic amines is described from the readily available γ-amino vinylic tin reagent 2, either by using the direct palladium catalysed coupling of the vinyl tin moitie or via conversion to a γ-amino vinyl lithium reagent.