109687-70-9Relevant articles and documents
Mild and selective silicon-mediated access to enantioenriched 1,2-mercaptoamines and β-amino arylchalcogenides
Tanini, Damiano,Borgogni, Cosimo,Capperucci, Antonella
supporting information, p. 6388 - 6393 (2019/04/25)
Metal-free ring opening reactions of activated and unactivated aziridines with different silyl chalcogenides are described. Judicious tuning of the reaction conditions enables the synthesis of chiral enantioenriched N-Ts and N-Boc 1,2-mercaptoamines in good yields from the corresponding aziridines and bis(trimethylsilyl)sulfide. N-Protected and N-H unactivated aziridines are efficiently converted into the corresponding β-arylchalcogeno amines upon treatment with suitable arylchalcogenosilanes. The silicon-mediated ring opening reactions proceed with excellent regioselectivity and stereospecificity, allowing to access a wide array of synthetically and biologically valuable enantioenriched chalcogenoamines.
Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters
Gul, Kashif,Narayanaperumal, Senthil,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
supporting information; experimental part, p. 3592 - 3596 (2011/07/31)
The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.
Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes
Granander, Johan,Sott, Richard,Hilmersson, Goeran
, p. 439 - 447 (2007/10/03)
Six chiral amino sulfides have been synthesised from the amino acids phenylalanine, phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with benzaldehyde, resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of >98.5 and 95%, respectively. These stereoselectivities were significantly higher than those induced by the ether analogues.