Amine-catalyzed addition of azide ion to alpha,beta-unsaturated carbonyl compounds.
[formula: see text] A new protocol for the beta-azidation of alpha,beta-unsaturated carbonyl compounds is described. The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for the reaction.
Guerin
D J
DJ
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.
Horstmann
T E
TE
Miller
S J
SJ
D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D007477:Ions; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D001386:Azides; D007477:Ions; D007659:Ketones