56424-42-1Relevant articles and documents
Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives
Guthrie, David B.,Damodaran, Krishnan,Curran, Dennis P.,Wilson, Paul,Clark, Andrew J.
supporting information; experimental part, p. 4262 - 4266 (2009/09/08)
(Chemical Equation Presented) Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.
Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, part IV. Relationship between ligand structure and enantioselectivity
Rossiter, Bryant E.,Eguchi, Masakatsu,Miao, Guobin,Swingle, Nicole M.,Hernandez, Amelia E.,Vickers, Denise,Fluckiger, Ezdan,Greg Patterson,Vasavi Reddy
, p. 965 - 986 (2007/10/02)
Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Nonlinear asymmetric induction was observed with the cuprate formed from ligand 13.
