Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones | Zendy

Fukuyama Takahide | Zendy; Ohta Yuko | Zendy; Brancour Célia | Zendy; Miyagawa Kazusa | Zendy; Ryu Ilhyong | Zendy; Dhimane AnneLise | Zendy; Fensterbank Louis | Zendy; Malacria Max | Zendy

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Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones

Author(s) -

Fukuyama Takahide,

Ohta Yuko,

Brancour Célia,

Miyagawa Kazusa,

Ryu Ilhyong,

Dhimane AnneLise,

Fensterbank Louis,

Malacria Max

Publication year - 2012

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201200045

Subject(s) - enyne , cycloaddition , moiety , chemistry , alkyne , catalysis , resorcinol , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry

We have developed novel Rh‐catalyzed [ n +1]‐type cycloadditions of 1,4‐enyne esters, which involve an acyloxy migration as a key step. The efficient preparation of functionalized resorcinols, including biaryl derivatives, from readily available 1,4‐enyne esters and CO was achieved by Rh‐catalyzed [5+1] cycloaddition accompanied by 1,2‐acyloxy migration. When enyne esters had an internal alkyne moiety, the reaction proceeded by a [4+1]‐type cycloaddition involving 1,3‐acyloxy migration, leading to cyclopentenones.

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