Pyrroles and Indolizidines
from Deprotonated α-(Alkylideneamino)nitriles

doi:10.1055/s-0030-1260415

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Synthesis 2011(11): 1691-1704
DOI: 10.1055/s-0030-1260415

FEATUREARTICLE

Pyrroles and Indolizidines from Deprotonated α-(Alkylideneamino)nitriles

Ines Schäfer^a,b, Till Opatz*^b
^a Department of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
^b Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3922338; e-Mail: opatz@uni-mainz.de;

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Publication History

Received 10 March 2011
Publication Date:
29 April 2011 (eFirst)

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Abstract

Their ready availability from simple starting materials in only two synthetic steps and their versatility as building blocks for the construction of highly substituted amines and N-heterocycles renders α-(alkylideneamino)nitriles useful synthetic intermediates. Herein, short syntheses of tri- and tetrasubstituted pyrroles including the northern half of the HMG-CoA reductase inhibitor atorvastatin as well as an access to 3-substituted indolizidines will be described.

Key words

heterocycles - carbanions - pyrroles - Umpolung - Michael addition