Rapid Construction of Cycloheptatriene through Organocatalyzed [4 + 3] Annulation of Coumalates.

Zhang, Haiyan; Han, Xiao; Chen, Tong; Wang, Zhen; Yao, Weijun

Zhang, Haiyan; Han, Xiao; Chen, Tong; Wang, Zhen; Yao, Weijun.

Afiliación

Zhang H; School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
Han X; School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
Chen T; School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
Wang Z; School of Pharmaceutical Sciences and Chongqing Key Laboratory of Natural Drug Research, Chongqing University, Chongqing 401331, P. R. China.
Yao W; School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.

Org Lett ; 26(36): 7495-7500, 2024 Sep 13.

Article en En | MEDLINE | ID: mdl-39235126

ABSTRACT

ABSTRACT

A protocol for the construction of cycloheptatrienes has been developed. 4-(Dimethylamino)pyridine (DMAP) was found to be an efficient catalyst to promote the [4 + 3] annulation between coumalates and Î³-alkyl-substituted allenoate or Î³-aryl-3-butynoates to deliver a variety of cycloheptatrienes in moderate to good yield with excellent chemoselectivity. The asymmetric version of this annulation was also realized by using bifunctional phosphine catalyst to provide the chiral products with 32-97% ee and 29-64% yield.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Estados Unidos

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