Synthesis 2011(11): 1691-1704
DOI: 10.1055/s-0030-1260415
DOI: 10.1055/s-0030-1260415
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New YorkPyrroles and Indolizidines from Deprotonated α-(Alkylideneamino)nitriles
Further Information
Received
10 March 2011
Publication Date:
29 April 2011 (eFirst)
Publication History
Publication Date:
29 April 2011 (eFirst)

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