96013-58-0Relevant academic research and scientific papers
The scope and regioselectivity of intramolecular N-C rearrangements of orthogonally protected sulfonamides, including cyclization to saccharin derivatives
Saidykhan, Amie,Ebert, Jenessa,Ally, Hashim,Gallagher, Richard T.,Martin, William H.C.,Bowen, Richard D.
supporting information, p. 3089 - 3091 (2017/07/18)
The scope and regiochemistry of the intramolecular N-C rearrangement involving ortholithiation of orthogonally protected sulfonamides in which an N-acyl or N-carboalkoxy group is transferred from nitrogen to the aromatic ring have been explored. Provided that excess lithium diisopropylamide is used, the process is compatible with the presence of acidic α-protons in a substituent attached to the aromatic ring or if the protons in the migrating acyl group are relatively inaccessible because of steric factors. In certain cases, the isolated product is not the ortho carboalkoxy species, but the derived saccharin; the regiochemistry found for starting materials containing a naphthalene ring is consistent with ortho lithiation at the most electron deficient position.
CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO N-TOSYLATED α, β-UNSATURATED AMIDES
Nagashima, Hideo,Ozaki, Nobuyasu,Washiyama, Masayoshi,Itoh, Kenji
, p. 657 - 660 (2007/10/02)
N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.).Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure.The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.
