102210-87-7Relevant academic research and scientific papers
Enantioselective diethylzinc addition to aromatic aldehydes catalyzed by novel Ti(IV) complex of three-dentate chiral sulfonamide ligands
Dabiri, Minoo,Salehi, Peyman,Heydari, Seddigheh,Kozehgary, Gholamreza
, p. 4350 - 4361 (2009)
The synthesis of several novel three-dentate sulfonamide alcohol ligands is described, starting from camphorsulfonyl chloride. The influence of temperature and ligand structure on the asymmetric addition of dietylzinc to aromatic aldehydes has been studied. Enantioselectivities up to 76% have been obtained.
Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles
Poornachandran, Mahalingam,Raghunathan, Raghavachary
, p. 6461 - 6474 (2008/09/21)
The 1,3-dipolar cycloaddition reactions of various N-tethered alkenyl aldehydes with some cyclic and acyclic amino acids have been studied. Some key sulfonamides having strategically positioned aldehyde and olefinic tether have been synthesized and effectively subjected to intramolecular azomethine ylide cycloaddition reaction resulting in a series of pyrrolo[3,4-b]pyrrole and its N-1-C-2 derivatives, and a series of novel heterotricyclic compounds, perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles, in good yields. The intramolecular cycloaddition reaction was found to be highly stereoselective to form only cis-fused cycloadducts in all cases.
Diastereoselective formation of 2-aryl-3-arenesulfonyl 4-ethyl-1,3-oxazolidines: An X-ray crystallographic and 1H NMR study
Biju Kumar,Patel, Hetal V.,Shah, Amrish C.,Trenkle, Markus,Cardin, Christine J.
, p. 3391 - 3396 (2007/10/03)
N-Arylsulfonamides of (R)- and (S)-2-amino-1-butanol, on condensation with aromatic aldehydes produced diastereomerically pure 2-aryl-3-arenesulfonyl 4-ethyl-1,3-oxazolidines. The absolute configurations of one enantiomeric pair have been determined from
Chirospecific Synthesis of (+)-Pilocarpine
Compagnone, Reinaldo S.,Rapoport, Henry
, p. 1713 - 1719 (2007/10/02)
An efficient chirospecific synthesis for (+)-pilocarpine (1a) using D-methionine or D-2-aminobutanol as chiral educt is described.Formation of the C3-C4 carbon bond at an early stage gave the key intermediate diethyl phosphonate.Wittig coupling of this phosphonate with 1-methyl-5-imidazolecarboxaldehyde introduced the imidazole moiety of the pilocarpine skeleton.Selective reduction of an α,β-unsaturated nitrile to the corresponding allylic alcohol, stereocontrolled hydrogenation of the olefin, and epimerization of (+)-isopilocarpine to (+)-pilocarpine via kinetic protonation led to formation of the natural alkaloid.This methodology allows chirospecific syntheses of the four possible stereoisomers of pilocarpine.A short and convenient route to (+/-)-pilocarpine based on the key intermediate phosphonate is also described.
