20218-56-8Relevant academic research and scientific papers
Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas
Lalonde, Mathieu P.,McGowan, Meredeth A.,Rajapaksa, Naomi S.,Jacobsen, Eric N.
, p. 1891 - 1894 (2013/04/10)
A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.
Utilization of industrial waste materials, 6: Utilization of derivatives of the bicyclic proline analog (all-R)-octahydrocyclopenta[b]pyrrol-2-carboxylic acid in the stereoselective synthesis
Wilken, Joerg,Wallbaum, Sabine,Saak, Wolfgang,Haase, Detlef,Pohl, Siegfried,Patkar, Laxmikant N.,Dixit, Arun N.,Chittari, Pabba,Rajappa, Srinivasachari,Martens, Juergen
, p. 927 - 934 (2007/10/03)
Utilization of the industrial waste material benzyl (all-R)-cyclopenta[b]pyrrol-2-carboxylate 1a or its derivatives 1b, 1c as chiral auxiliaries is described. Allylation of nitrothioacetamides, proceeding by initial S-allylation followed by a facile thio Claisen rearrangement, is accomplished with a diastereomeric ratio (dr) up to 85:15 using 1a, b as auxiliaries in stoichiometric amounts. Another aspect of this report is the diastereoselective synthesis of optically active amines, starting from aldehydes, with optical purities (op) up to 99%. Again a derivative of 1a was used as source of chirality. VCH Verlagsgesellschaft mbH, 1996.
Asymmetric induction by chiral heterocyclic compounds: highly diastereoselective reaction of 5-oxa-7,8a-diazaperhydroazulen-8-ones with organometallic reagents
Takahashi, Hiroshi,Morimoto, Ichiro,Higashiyama, Kimio
, p. 287 - 290 (2007/10/02)
1) New chiral heterocyclic compounds, 5-oxa-7,8a-diazaperhydroazulen-8-ones (3a-c), were synthesized from (S)-prolinol (1) and potassium cyanate, followed by the condensation with aldehydes. 2) Extremely high diastereoselective reaction of the 3a-c with diethylzinc proceeded with a facil procedure to give (2S,1'S)-N-1'-arylpropyl-2-hydroxymethyl-1-pyrrolidinecarboxamide (4a-c). 3) The reduction of 4a-c with Red-Al gave (S)-1-aryl-N-methylpropylamines (5a-c) and (S)-prolinol (1) in good yields.
