Phosphine-Catalyzed (4 + 2) Annulation of Allenoates with Benzofuran-Derived Azadienes and Subsequent Thio-Michael Addition.

Wangyu Shi, Yue Ren, Haoran Zhao, Yi Tang, Shixiang Piao, Biming Mao, Wei Wang, Yongjun Wu, Bo Wang, Hongchao Guo

Organic letters 2022 May 27

filter terms:

A phosphine-catalyzed (4 + 2) annulation of tetrahydrobenzofuranone-derived allenoates and benzofuran-derived azadienes (BDAs) has been achieved to construct the decahydro-2H-naphtho[1,8-bc]furan derivatives, which were subsequently treated with 4-methylbenzenethiol and trimethylamine to produce thio-Michael addition products in high to excellent yields with good diastereoselectivities.

Citation

Wangyu Shi, Yue Ren, Haoran Zhao, Yi Tang, Shixiang Piao, Biming Mao, Wei Wang, Yongjun Wu, Bo Wang, Hongchao Guo. Phosphine-Catalyzed (4 + 2) Annulation of Allenoates with Benzofuran-Derived Azadienes and Subsequent Thio-Michael Addition. Organic letters. 2022 May 27;24(20):3747-3752