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Phosphine-catalyzed intramolecular ?-umpolung addition of ?-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines.

ABSTRACT: An array of N-tosylated ?-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The ?-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 ?-umpolung addition.

SUBMITTER: Andrews IP 

PROVIDER: S-EPMC4128507 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines.

Andrews Ian P IP   Blank Brian R BR   Kwon Ohyun O  

Chemical communications (Cambridge, England) 20120423 43

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. ...[more]

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