192461-71-5Relevant academic research and scientific papers
Synthesis of new chiral catalysts, N-alkyl-2-azanorbornyl-methanols, for the enantioselective addition of diethylzinc to arylaldehydes
Nakano,Kumagai,Kabuto,Matsuzaki,Hongo
, p. 1233 - 1236 (1995)
New chiral ligands, 2-azanorbornylmethanols, were prepared and catalyzed the addition of diethylzinc to arylaldehydes to furnish secondary alcohols in up to 92% ee.
endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction
Bassani, Marco,Scarso, Alessandro,Drago, Maria,Zambon, Alfonso,Fabris, Fabrizio
supporting information, (2020/07/10)
We report the synthesis and preliminary evaluation of (1S,2S,4R)-7,7-dimethyl-1-phenylbicyclo[2.2.1]heptan-2-ol 1a, which was obtained in 3 steps from inexpensive starting materials, as a chiral auxiliary. The potential for asymmetric induction was investigated by carrying out aza-Diels-Alder reactions with cyclopentadiene and imine derivatives of 1a from (R)-(+)-1-phenylethylamine, (S)-(?)-1-phenylethylamine and benzylamine. The results showed marked exo selectivity and good diastereoisomeric excess when 1a was combined with (R)-(+)-1-phenylethylamine. These results are comparable with those reported using (?)-8-phenylmenthol, suggesting that 1a can represent an economically viable alternative to current chiral auxiliaries.
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
