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Issue 43, 2012
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Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

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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 Ph3P-catalyzed intramolecular γ-umpolung addition.

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

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Article information


Submitted
23 Feb 2012
Accepted
23 Mar 2012
First published
23 Apr 2012

Chem. Commun., 2012,48, 5373-5375
Article type
Communication

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

I. P. Andrews, B. R. Blank and O. Kwon, Chem. Commun., 2012, 48, 5373
DOI: 10.1039/C2CC31347B

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