139927-14-3Relevant academic research and scientific papers
Epibatidine alkaloid chemistry: 5. Domino-heck reactions of azabicyclic and tricyclic systems
Yolacan, Cigdem,Bagdatli, Emine,Oecal, Nueket,Kaufmann, Dieter E.
, p. 603 - 614 (2007/10/03)
Palladium-catalyzed hydroarylations and additional domino reactions of azabicyclic and tricyclic norbornene derivatives were investigated and a series of new epibatidine analogues were synthesized.
Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid
Arakawa, Yasushi,Yasuda, Mika,Ohnishi, Masafumi,Yoshifuji, Shigeyuki
, p. 255 - 259 (2007/10/03)
Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.
A Novel Skeletal Rearrangement of 2-Azabicyclohept-5-ene-3-carboxylic Acid Derivatives into 2-Oxabicyclo-oct-7-en-3-ones under Acidic Conditions
Kobayashi, Tomoshige,Ono, Katsuhiko,Kato, Hiroshi
, p. 61 - 65 (2007/10/02)
The reaction of ethyl 2-azabicyclohept-5-ene-3-carboxylate with aroyl chloride and the subsequent hydrolysis of the ester group provided 2-aroyl-2-azabicyclohept-5-ene-3-carboxylic acid derivatives, which underwent a stereospecific rearrange
Nitrenium and Carbenium Ions in Rearrangements of 2-Azabicyclic Systems
Heesing, Albert,Herdering, Wilhelm
, p. 1081 - 1096 (2007/10/02)
An ionic mechanism proceeding in intimate ion pairs is suggested for the rearrangement of N-sulfonyloxy derivatives of 2-azabicycloheptane and -hept-5-ene (e. g. 9, 11 -> 10, 12). 1.Experiments with 18O labelled educts show partial scrambling dependend both on structure of educt and solvent. 2.In methanol the intermediate carbenium ions (19, 23) react to give methoxy compounds. 3.MINDO/3-calculations are in agreement with the experiments: a) In the saturated systems the nitrenium ion 20 is a stable intermediate. b) The optimized geometries of the rearranged carbenium ions (21, 23) are consistent with the products obtained in methanol.
