105526-88-3Relevant academic research and scientific papers
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 (1995)
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.
Highly diastereoselective conjugate additions of monoorganocopper reagents to chiral imides
Dambacher, Jesse,Anness, Robert,Pollock, Patrick,Bergdahl, Mikael
, p. 2097 - 2110 (2007/10/03)
Stereoselective conjugate additions to chiral N-enoyl amides employing various monoorganocuprate reagents, Li[RCuI], are described. The presence of TMSI in the addition of Li[RCuI] in THF provided the highest stereoselectivities. Reversed major diastereom
ASYMMETRIC CONJUGATE ADDITION REACTION BY THE USE OF (S)-γ-TRITYLOXYMETHYL-γ-BUTYROLACTAM AS A CHIRAL AUXILIARY
Tomioka, Kiyoshi,Suenaga, Toshiro,Koga, Kenji
, p. 369 - 372 (2007/10/02)
(S)-γ-Trityloxymethyl-γ-butyrolactam (2) serves as a chiral auxiliary in the conjugate addition reaction of the corresponding imide (3) of α,β-unsaturated carboxylic acids with Grignard reagents in the presence of CuBr-SMe2 in THF to give, after hydrolysis, the β,β-disubstituted carboxylic acids (5) with predictable absolute configuration and high enantiomeric excess.
