Sc(OTf) 3 ‐Catalyzed Diastereoselective Formal [3+2] Cycloaddition Reactions of Alkynylcyclopropane Ketones with Electron‐Rich Aromatic Aldehydes To Yield 2,5‐ trans ‐Tetrahydrofurans | Zendy

Zhang Chi | Zendy; Xu Muyun | Zendy; Ren Jun | Zendy; Wang Zhongwen | Zendy

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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.

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