62281-29-2Relevant articles and documents
Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines
Huang, Li,Zhang, Yu,Staples, Richard J.,Huang, Rui H.,Wulff, William D.
supporting information; experimental part, p. 5302 - 5313 (2012/05/20)
The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.
Cobalt carbonyl catalyzed reaction of mercaptans with Schiff bases and carbon monoxide
Antebi, Shlomo,Alper, Howard
, p. 2010 - 2012 (2007/10/02)
Thiophenols and p-methylbenzyl mercaptan react with Schiff bases and carbon monoxide in benzene, in the presence of cobalt carbonyl, to give amides as the pricipal products.These amides arise from cleavage of the carbon-nitrogen double bond of the reactant imine.The reaction is applicable to a variety of Schiff bases (i.e. aliphatic, benzylic, aromatic).Thioesters and olefins are usually obtained as reaction by-products.
