36101-18-5Relevant academic research and scientific papers
Synthesis of new chiral 1,3-aminoalcohols derived from levoglucosenone and their application in asymmetric alkylations
Zanardi, María M.,Suárez, Alejandra G.
, p. 3762 - 3765 (2015)
We have developed a simple procedure for the preparation of chiral 1,3-aminoalcohols using the biomass derivative levoglucosenone, as the chiral starting material. 1,3-aminoalcohols, bearing primary and tertiary amino groups, were tested as chiral catalysts in the asymmetric addition of diethyl zinc to benzaldehyde.
Asymmetric control in Diels-Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information
Adams, Harry,Bawa, Ramadan A.,McMillan, Keith G.,Jones, Simon
, p. 1003 - 1012 (2008/02/03)
Two approaches to the synthesis of chiral 9-amino anthracenes are described. The first, by nucleophilic addition of organolithium reagents to imines promoted by BF3·OEt2, unexpectedly provided stable aminoboranes as products. The second approach, using palladium catalysed cross coupling, was more successful for primary amines, and the key 9-(α-methylbenzylamino)anthracene subjected to cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels-Alder reaction of these cycloadducts were also performed.
