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Ag(I) Catalyzed Cascade Approach to 2‐(α‐Hydroxyacyl)pyrroles
Author(s) -
Gandhi Soniya,
Baire Beeraiah
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700514
Subject(s) - catalysis , cascade , primary (astronomy) , chemistry , pyrrole , combinatorial chemistry , cascade reaction , organic chemistry , chromatography , physics , astronomy
A mild cascade approach for the generation of 2‐(α‐hydroxyacyl)pyrroles under Ag(I) catalysis has been reported. This strategy involves a 5‐ exo‐dig cyclization of insitu generated imines from 6‐hydroxyhex‐2‐en‐4‐ynals and primary amines followed by oxidation. The reaction is very general for propargylic alcohols, tethers and primary amines. Efficient synthesis of core structures of pyrrole based bioactive natural products have also been achieved. Control experiments revealed the fact that, presence of excess oxygen and water may favor the competitive formation of the furans over the pyrroles.