Organic Letters
Organic Letters
5 years ago

Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams

Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams
Chunjie Ni, Jiangfei Chen, Xiaofeng Tong, Yuwen Zhang, Shou-Fei Zhu, Yading Hou, Qi-Lin Zhou, Dong Wang
While the phosphine catalysis is a powerful tool for the construction of N-heterocycles, the phosphine-catalyzed annulations toward lactam motif are still extremely scarce. Here, we report the asymmetric (3 + 2) annulations of δ-acetoxy allenoates with β-carbonyl amides by using the (R)-SITCP catalyst. The δC and γC of allenoate respectively engage in annulation with the αC and N of the amide, forging a γ-lactam with good to excellent stereoselectivity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01717

DOI: 10.1021/acs.orglett.7b01717

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