202280-61-3Relevant academic research and scientific papers
Electronic and steric control in regioselective addition reactions of organolithium reagents with enaldimines
Tomioka,Shioya,Nagaoka,Yamada
, p. 7051 - 7054 (2007/10/03)
A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic α,β-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nirtogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1,4-addition of organolithium reagents. Electronic and steric tuning of a substituent on the imine nitrogen atom for a reaction mode was rationalized on the basis of molecular orbital calculations.
Regioselective addition reaction of organolanthanide reagents to α,β-unsaturated imines
Qian, Changtao,Huang, Taisheng
, p. 143 - 147 (2007/10/03)
Organolanthanum reagents[RLaCl2] generated in situ from LaCl3 and alkyl lithium or allyl magnesium could undergo a highly regioselective 1,2-addition to N-alkyl α,β-unsaturated imines, which provided a new and useful approach to synthesize allyl amines with good yields and high regioselectivity. Furthermore, for N-chiral alkyl α,β-unsaturated imine, in the case of n-butyl lithium, the diastereoselectivity achieved highly 90%.
