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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Organocatalytic Asymmetric Formal [2 + 1] Cycloaddition Reactions for the Synthesis of Spiro-cyclopropane-pyrazolones
Khushboo Gupta1, Chhavi Khajuria1, Nidhi Saini1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh208 016, India.
Abstract:
Herein, we have developed an efficient and highly enantioselective approach for the synthesis of spiro-cyclopropane-pyrazolones via a proline-based secondary amine-catalyzed formal [2 + 1] cycloaddition reaction. The protocol provides access to structurally diverse spiro-cyclopropane-pyrazolone derivatives bearing three contiguous stereogenic centers in good to excellent diastereoselectivities and excellent enantioselectivities. Mechanistic studies support the proposed reaction pathway, while the scalability of the reaction further demonstrates its practical utility.
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