177780-87-9Relevant academic research and scientific papers
Synthesis of medium and large cyclic amines in rhodium-catalysed reactions of aminoalkenes with H2/CO1
Bergmann, David J.,Campi, Eva M.,Roy Jackson,Patti, Antonio F.,Saylik, Dilek
, p. 835 - 844 (2007/10/03)
Rhodium-catalysed reactions of N-benzyl- or N-alkyl-aminoalkenes (6) with H2/CO can give cyclic amines (7) (7-13 ring size) in good to excellent yields when BIPHEPHOS is used as a ligand. Hydrogenation of the aminoalkene becomes a competing reaction for the smaller rings but can be overcome by using a H2/CO gas ratio of 1:5. Reactions of 2-alkenyloxybenzylamines (13) gave 9-, 12- and 17-membered rings (14) in 30-40% yield, but dimer formation (16) and/or hydrogenation were competing reactions. Similar reactions of alkenylamides and ortho-alkenylanilines gave only non-cyclized amino aldehydes as products in low isolated yields.
The stereochemistry of organometallic compounds. XLIII* rhodium-catalysed reactions of 2-(alkenyloxy)benzylamines and 2-(N-allyl-N-benzylamino)benzylamine
Campi, Eva M.,Jackson, W. Roy,McCubbin, Quentin J.,Trnacek, Andrew E.
, p. 219 - 230 (2007/10/03)
Reactions of 2-(allyloxy)benzylamines with H2/CO in the presence of rhodium catalysts give 1,3-benzoxazines, and 2-(N-allyl-N-benzylamino)benzylamine gives a quinazoline. These reactions have been shown to involve allylic cleavage followed by regioselective carbonylation at the internal carbon atom as demonstrated by crossover experiments. Reactions of longer chain (alkenyloxy)benzylamines under similar conditions give polymeric material.
