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Sc(OTf) 3 ‐Catalyzed Diastereoselective Formal [3+2] Cycloaddition Reactions of Alkynylcyclopropane Ketones with Electron‐Rich Aromatic Aldehydes To Yield 2,5‐ trans ‐Tetrahydrofurans
Author(s) -
Zhang Chi,
Xu Muyun,
Ren Jun,
Wang Zhongwen
Publication year - 2016
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.201600233
Subject(s) - cycloaddition , chemistry , tetrahydrofuran , yield (engineering) , catalysis , intermolecular force , medicinal chemistry , domino , stereochemistry , organic chemistry , molecule , materials science , solvent , metallurgy
In contast to the general [4+2] cycloaddition reactions of alkynylcyclopropane ketones reported in the literature, we report herein a Sc(OTf) 3 ‐catalyzed formal intermolecular [3+2] cycloaddition reaction of alkynylcyclopropane ketones with electron‐rich aromatic aldehydes. 2,3,3,5‐Tetrasubstituted tetrahydrofurans were obtained by this method, and the tetrahydrofuran skeleton was diastereoselectively constructed with a 2,5‐ trans configuration. This is also quite different to the 2,5‐ cis configuration usually obtained from typical [3+2] cycloaddition reactions of most donor–acceptor cyclopropanes. Additionally, the cycloadducts were subjected to a domino carbopalladation/C–H activation/C–C bond‐formation process for the highly efficient construction of polycyclic skeletons.