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Vinylogous Annulation Cascade Toward Stereoselective Synthesis of Highly Functionalized Indanone Derivatives
Author(s) -
Bhajammanavar Vinod,
Mallik Sumitava,
Baidya Mahiuddin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900860
Subject(s) - annulation , chemistry , cyclopentene , stereoselectivity , combinatorial chemistry , cascade , ring (chemistry) , coumarin , cascade reaction , stereochemistry , derivative (finance) , surface modification , organic chemistry , catalysis , chromatography , financial economics , economics
A base promoted vinylogous annulation cascade of alkylidene malononitriles with cyclopentene‐1,3‐diones with a subsequent reduction sequence has been devised to furnish densely functionalized 3‐hydroxyindanone scaffolds in high yields with excellent diastereoselectivity. Unlike preceding approaches that account for the formation of the pentanoid ring, this strategy features construction of the aromatic ring. The protocol is scalable, displays very broad substrates scope including late‐stage functionalization of bioactive estrone, applicable to activated coumarin system, and is suitable to access an indenoquinoline derivative.