211503-92-3Relevant articles and documents
Stereoselective Conjugate Addition of the Lithium Anion of N-Allyl Imine to Unsaturated Esters: Application to the Enantiospecific Total Synthesis of (-)-Epibatidine
Prasad, Kavirayani R.,Uphade, Manoj B.
, p. 9648 - 9660 (2019/08/20)
A regio- and diastereoselective conjugate addition of the lithium anion of N-allyl imine (prepared from allylamine and benzophenone) to α,β-unsaturated esters in good yields is reported. The reaction was general and provided the γ-amino esters resulting from the regioselective C-C bond formation between the α-carbon to the nitrogen in the imine and the β-carbon of the unsaturated ester. Synthetic utility of the formed products was illustrated in the nonracemic total synthesis of the bioactive alkaloid (-)-epibatidine.
Synthesis of (-)-epibatidine
Evans, David A.,Scheidt, Karl A.,Downey, C. Wade
, p. 3009 - 3012 (2007/10/03)
matrix presented The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement.
Asymmetric total synthesis of (-)-epibatidine
Aoyagi, Sakae,Tanaka, Ryuta,Naruse, Masaichi,Kibayashi, Chihiro
, p. 4513 - 4516 (2007/10/03)
An enantioselective approach to (-)-epibatidine based on asymmetric hetero Diels-Alder cycloaddition with an N-acylnitroso dienophile bearing 8- (2-naphthyl)menthol as a chiral source, wherein π-π stacking interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control, is described.