255916-69-9Relevant academic research and scientific papers
Stereodynamics of bond rotation in tertiary aromatic amides
Bragg, Ryan A.,Clayden, Jonathan,Morris, Gareth A.,Pink, Jennifer H.
, p. 1279 - 1289 (2007/10/03)
The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymm
'meso-Selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation
Bragg, Ryan A,Clayden, Jonathan,Menet, Christel J
, p. 1955 - 1959 (2007/10/03)
Lithiation and methylation of amide and carbamate derivatives of α-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-α-methylbenzylamine derivatives. Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-α-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability.
Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations
Bragg, Ryan A.,Clayden, Jonathan
, p. 8323 - 8326 (2007/10/03)
Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.
