95587-14-7Relevant articles and documents
Enantioselective syntheses of 2-substituted pyrrolidines from allylamines by domino hydroformylation-condensation: Short syntheses of (S)-nicotine and the alkaloid 225C
Dübon, Pierre,Farwick, Andreas,Helmchen, Günter
scheme or table, p. 1413 - 1416 (2009/10/23)
Short routes to chiral 2-substituted pyrrolidines based on rhodium-catalyzed hydroformylations of allylamines and their N-alkyl and N-acyl derivatives, which were prepared by asymmetric allylic substitutions, are described. The outcome of the hydroformyla
Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene- based transformations for the syntheses of naturally occurring alkaloids
Arredondo, Victor M.,Tian, Shun,McDonald, Frank E.,Marks, Tobin J.
, p. 3633 - 3639 (2007/10/03)
The total syntheses of the pyrrolidine alkaloid (+)-197B (1) and pyrrolizidine alkaloid (+)-xenovenine (2) are described. The strategy involves enantioselective syntheses of the aminoallene, (5S,8S)-5-amino- trideca-8,9-diene (3), and the aminoallene-alkene, (5S)-5-amino-pentadeca- 1,8,9-triene (4), which then undergo regio- and stereoselective cyclohydroamination catalyzed by the organolanthanide precatalysts Cp'2LnCH(TMS)2 and Me2SiCp''((t)BuN)LnN(TMS)2 (Cp' = η5-Me5C5; Cp'' = η5-Me4C5; Ln = lanthanide; TMS = Me3Si). These reactive organolanthanide complexes efficiently mediate highly diastereoselective intramolecular hydroamination/cyclization (IHC) reactions under mild conditions. The turnover-limiting step in these catalytic cycles is proposed to be intramolecular insertion into the Ln-N bond of the proximal allenic C=C linkage, followed by rapid protonolytic cleavage of the resulting Ln-C bond. The rate and selectivity of the insertion process is highly sensitive to the steric demands of the substrate.
ASYMMETRIC SYNTHESIS XII: STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC α,α'-SUBSTITUTION OF THE PYRROLIDINE RING.
Arseniyadis, S.,Huang, P. Q.,Piveteau, D.,Husson, H.-P.
, p. 2457 - 2470 (2007/10/02)
The synthesis of 2-cyano-5-oxazolopyrrolidine 3, a chiral pyrrolidine synthon, is described.Conditions were established that permitted sequential chemoselective reactions at the C-2 aminonitrile (electrophilic substitution) and at the C-5 aminoether (nucl