3 years ago

PPh3-Catalyzed [3 + 2] Spiroannulation of 1C,3N-Bisnucleophiles Derived from Secondary β-Ketoamides with δ-Acetoxy Allenoate: A Route to Functionalized Spiro N-Heterocyclic Derivatives

PPh3-Catalyzed [3 + 2] Spiroannulation of 1C,3N-Bisnucleophiles Derived from Secondary β-Ketoamides with δ-Acetoxy Allenoate: A Route to Functionalized Spiro N-Heterocyclic Derivatives
Yu-Ning Gao, Jiaojiao Xing, Yu Lei, Min Shi
A [3 + 2] annulation of α-substituted secondary β-ketoamides with δ-acetoxy-modified allenoate has been developed in the presence of phosphine catalyst. In this spiroannulation reaction, β-ketoamides were used as the bis-nucleophilic partner while the γ,δ-carbon of 5-acetoxypenta-2,3-dienoate participated as a C2 synthon, affording the desired functionalized five-membered N-heterocyclic derivatives in moderate to excellent yields and diastereoselectivities under mild conditions. Preliminary attempts on the asymmetric variant of this reaction have been also examined, giving the corresponding products with moderate ee values.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00910

DOI: 10.1021/acs.orglett.7b00910

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