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Catalyst‐Controlled Ring‐Opening Cycloisomerization Reactions of Cyclopropenyl Carboxylates for Highly Regioselective Synthesis of Different 2‐Alkoxyfurans
Author(s) -
Chen Jie,
Ma Shengming
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000324
Subject(s) - cycloisomerization , regioselectivity , ring (chemistry) , catalysis , chemistry , medicinal chemistry , stereochemistry , organic chemistry
Differently substituted 2‐alkoxyfurans (2,3,4‐ or 2,3,5‐trisubstituted furans) were highly regioselectively synthesized by means of the ring‐opening cycloisomerization of the same cyclopropenyl carboxylates with good yields in different solvents and excellent regioselectivity by using [Cu(acac) 2 ] (acac=acetylacetonate) or [RuCl 2 (PPh 3 ) 3 ] as the catalyst, respectively. The structures of these two different types of furans were established by X‐ray diffraction studies. A rationale has been proposed.