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In Situ Generation of Allenes and their Application to One‐Pot Assembly of Functionalized Fluoreno[3,2‐ b ]furans by Calcium‐Catalyzed, Regioselective, 3‐Component Reactions
Author(s) -
Yaragorla Srinivasarao,
Rajesh Pallava
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001310
Subject(s) - chemistry , regioselectivity , propargyl , annulation , catalysis , combinatorial chemistry , substrate (aquarium) , surface modification , organic chemistry , cascade reaction , oceanography , geology
We have developed a novel synthetic methodology for the preparation of tetra‐annulated fluorenofurans and fluorenopyrans using calcium(II)‐catalyzed one‐pot, three‐component reaction. In this reaction, tert ‐propargyl alcohols react with 1,3‐dicarbonyls to form tetra‐substituted allenes, which are subsequently undergoing regiodivergent annulation with sec ‐propargyl alcohols to produce the fluorene‐fused furan compounds. Broad substrate scope, regioselectivity, gram‐scale synthesis, and benzylic functionalization of products are some of the highlights of this protocol.