192461-74-8Relevant academic research and scientific papers
The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction
Cardoso do Vale, Maria Luísa,Rodríguez-Borges, José Enrique,Caama?o, Olga,Fernández, Franco,García-Mera, Xerardo
, p. 9475 - 9482 (2007/10/03)
The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.
Enantioselective addition of diethylzinc to aldehydes using 2-azanorbornylmethanols and 2-azanorbornylmethanethiol as a catalyst
Nakano, Hiroto,Kumagai, Noriyuki,Matsuzaki, Hisao,Kabuto, Chizuko,Hongo, Hiroshi
, p. 1391 - 1401 (2007/10/03)
Optically active 2-azanorbornylmethanols and 2-azanorbomylmethanethiol were prepared from ethyl (1S,3S,4R)-2-[(R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene- 3-carboxylate and catalyzed the enantioselective addition of diethylzine to aldehydes to give o
