Details

Autor(en) / Beteiligte

• Lai, Jingxiong
• Huang, You

Titel

A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CHOK

Ist Teil von

• Chemical communications (Cambridge, England), 2024-02, Vol.6 (15), p.266-269

Erscheinungsjahr

2024

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The first (5+1) annulation of allenoates and pyrazolones catalyzed by CH 3 OK has been reported. A series of spiro-pyrazolone derivatives were obtained as single diastereomers in high yields (≤95%) under mild conditions. The synthetic utility was demonstrated by a scale-up reaction and various transformations of the products. The proposed mechanism suggests that the allenoate works as a 1,5-biselectrophilic 5C synthon for the first time and controlled experiments disclose that K + plays an important role in the diastereoselectivity-determining step through an eight-membered ring transition state. Also, this 1,5-biselectrophilic allenoate will be able to act as a 5C synthon for (5+ n ) annulation. A CH 3 OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.