314249-76-8Relevant academic research and scientific papers
A new chiral masked form of glyoxal diimine
Martelli, Gianluca,Savoia, Diego
, p. 1531 - 1540 (2003)
(3R,4R,5R,6R)-3,6-Diphenyl-N,N′-bis[(S)-1-phenylethyl]octa-1, 7-diene-4,5-diamine, by treatment with organolithium reagents RLi in controlled experimental conditions, underwent rearrangement and/or substitution of one or two branched allyl(s) by the R group(s). Hence, this diene behaves as a masked form of the chiral glyoxal diimine from that it is prepared, allowing the preparation of C1-symmetric 1,2-disubstituted 1,2-diamines, which are generally not available by the direct addition of organometallic reagents to the diimine, and C2-symmetric 1,2-diamines with good diastereoselectivities.
Synthesis of chiral C2-symmetric 1,2-diamines by the addition of organolithium reagents to N,N'-bis[(S)-1-phenylethyl]ethanediimine
Martelli, Gianluca,Morri, Stefano,Savoia, Diego
, p. 8367 - 8374 (2007/10/03)
The additions of alkyl-, phenyl- and vinyllithium reagents to N,N'-bis[(S)-1-phenylethyl]ethanediimine in THF at -78°C and in DME at -60°C gave high yields of 1,2-diamines with low stereocontrol. Care was taken to quench the reaction mixtures with de-aera
