3 years ago

Preparation of 2-Amino-5-homoallylfurans via Palladium-Catalyzed Tandem Cycloisomerization/Heck-Type Coupling of Homoallenyl Amides with Allyltrialkylsilanes

Preparation of 2-Amino-5-homoallylfurans via Palladium-Catalyzed Tandem Cycloisomerization/Heck-Type Coupling of Homoallenyl Amides with Allyltrialkylsilanes
Cungui Cheng, Mingchang Wu, Jian Zhang, Gangguo Zhu, Wei Lu, Shuaifeng Wang, Yan Zhang
The direct access to 2-amino-5-homoallylfurans has been realized by a palladium-catalyzed tandem cycloisomerization/Heck-type coupling between homoallenyl amides and allyltrialkylsilanes, using a novel DDQ/MnO2 combination as the efficient oxidant. The reaction exclusively affords γ-allylation products in good to excellent yields with broad substrate scope under exceptionally mild reaction conditions. It represents one of the rare examples of the Pd-catalyzed intermolecular Heck-type coupling of allytrialkylsilanes terminated by β-silyl elimination, thus complementing traditional allylation methods because of the excellent γ-selectivity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02131

DOI: 10.1021/acs.joc.7b02131

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