80865-98-1Relevant academic research and scientific papers
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.
β-Substituted Organolithium Compounds. Reaction with Alkyl Halides, Dimethyl Disulfide, and Imines
Barluenga, Jose,Fananas, Francisco J.,Villamana, Jorge,Yus, Miguel
, p. 1560 - 1564 (2007/10/02)
The reaction of β-substituted organolithium derivatives with several electrophiles leads to mono- as well as bifunctionalized organic compounds.Thus, by treatment of these dianions with alkyl halides a direct attack on the carbanionic carbon atom is performed, giving as a result substituted amines.When dimethyl disulfide is used, β-amino and β-hydroxy thioethers are obtained.Finally, on reaction with imines, 1-amino-3-hydroxy compounds and 1,3-diamines are obtained.Since these dianions are easily preparated by mercury-lithium transmetalation from β-substituted organomercurials resulting from the addition of mercury(II) salts to olefins, this whole process gives an appropriate way of functionalizing olefins.
