23099-29-8Relevant articles and documents
Naphthalene-Catalysed Reductive Opening of Aziridines with Lithium: A Direct Preparation of N-Lithio-2-lithioalkylamines
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 1649 - 1652 (1993)
The reductive opening of N-phenylaziridine (1) with an excess of lithium powder in the presence of a catalytic amount (5 molar percent) of naphthalene at -78 deg C leads to the corresponding N-lithio-2-lithioethylamine (2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected products 3.The same process applied to N-cyclohexylaziridine fails.The reaction also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.
N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 3210 - 3215 (2007/10/02)
The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 deg C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents , (EtO)2CO, CH2=CHCO2Me, , PhCH=NPh, MeI, and CH2=CHCH2Br> to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5.When the reductive opening and the reaction with electrophiles were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with the same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
