title: Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines.
abstract: An array of N-tosylated α-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The α-aminoalkylallenic esters were prepared through aza-Baylis-Hillman reactions or novel DABCO-mediated decarboxylative rearrangements of allenylic carbamates. Conversion of these substrates to 3-carbethoxy-2-alkyl-3-pyrrolines was facilitated through Ph(3)P-catalyzed intramolecular γ-umpolung addition.
authors.affiliation: ohyun@chem.ucla.edu
authors.forename: Ian P
authors.initials: IP
authors.lastname: Andrews
authors.forename: Brian R
authors.initials: BR
authors.lastname: Blank
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D007536:Isomerism; D010720:Phosphines / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000588:Amines; D004952:Esters; D010720:Phosphines; D010879:Piperazines; D011758:Pyrroles; C013231:pyrroline; C044646:phosphine; C007306:triethylenediamine