98314-62-6Relevant articles and documents
Amidation of esters with amino alcohols using organobase catalysis
Caldwell, Nicola,Campbell, Peter S.,Jamieson, Craig,Potjewyd, Frances,Simpson, Iain,Watson, Allan J. B.
, p. 9347 - 9354 (2014/12/11)
A catalytic protocol for the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.
Diastereoselectivity in Iodotrimethylsilane-promoted Conjugate Additions of Organocopper Reagents to Chiral α,β-Unsaturated Imides and Amides
Bergdahl, Mikael,Iliefski, Tommy,Nilsson, Martin,Olsson, Thomas
, p. 3227 - 3230 (2007/10/02)
Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90percent and diastereoselectivities from 80 to 93percent.The dominating diastereomers are different from those formed with LiR2Cu/TMSCl or in copper(I)-mediated addition of Grignard reagents.Corresponding additions to enoyl-amides of O-tritylprolinol also give high yields of conjugate adducts, but lower diastereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.
A Method for the Preparation of Stereochemically Defined ψ Pseudodipeptides
TenBrink, Ruth E.
, p. 418 - 422 (2007/10/02)
A short, stereochemically defined synthesis of (2S,5S)-ψ pseudodipeptides (7a,7b,10) using commercially available, chiral amino acids has been developed.The key step of the synthesis is the intramolecular SN2 displacement of bromine with alkoxide to give 1,4-oxazin-2-ones (6a,6b,9) that are subsequently hydrolyzed to the desired ψ pseudodipeptides.
