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Knoevenagel‐Friedel‐Crafts‐Hemiketalization Triple Cascade Reaction: A Diastereoselective Formal [1+2+3] Cyclization Towards Indenonaphthopyran Scaffolds
Author(s) -
Settipalli Poorna Chandrasekhar,
Reddy Yeruva Pavankumar,
Gudise Veera Babu,
Anwar Shaik
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004619
Subject(s) - knoevenagel condensation , stereocenter , aldehyde , chemistry , cascade reaction , substrate (aquarium) , friedel–crafts reaction , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , enantioselective synthesis , oceanography , geology
A simple and efficient cascade reaction via formal [1+2+3] cyclization of 1,3‐indanedione, aldehyde and 2‐naphthol is reported using K 2 CO 3 as a base. The advantage includes metal‐free conditions, varied substrate scope and shortened reaction duration with high diastereoselectivity (i. e., 99 : 1) resulting in the formation of two carbon‐carbon as well as two carbon‐oxygen bonds through Knoevenagel‐Friedel‐Crafts‐Hemiketalization sequence resulting in three contiguous stereocenters.