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Calcium(II) Catalyzed Cycloisomerization of cis ‐6‐Hydroxy/(Acyloxy)hex‐2‐en‐4‐ynals to 2‐Acyl‐ and 2‐(Acyloxyalkenyl)furans
Author(s) -
Gandhi Soniya,
Baire Beeraiah
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800618
Subject(s) - cycloisomerization , chemistry , catalysis , furan , atom economy , calcium , substrate (aquarium) , bicyclic molecule , stereochemistry , reaction conditions , medicinal chemistry , combinatorial chemistry , organic chemistry , oceanography , geology
A cycloisomerization reaction of cis ‐6‐hydroxy and cis ‐6‐acyloxyhex‐2‐en‐4‐ynals to 2‐acylfurans and 2‐(1‐acyloxyalkenyl)furans under calcium(II) catalysis is reported. This strategy allows for the efficient synthesis of 3,4‐fused bicyclic 2‐acylfurans, multi‐substituted 2‐acylfurans and structurally novel 2‐(acyloxyalkenyl)furan derivatives which are substructures of many bioactive natural products. Very broad and divergent substrate scope with respect to propargylic alcohols and linkers has been achieved. The transformation fulfils some of the green chemistry principles in terms of a) use of non‐toxic, biodegradable calcium, b) 100% atom economy, and c) catalytic process and mild reaction conditions (RT).