Diastereoselective access to [4, 4]-carbospirocycles: governance of thermodynamic enolates with an organocatalyst in vinylogous cascade annulation. Issue 13 (24th January 2022)

• Record Type: Journal Article
• Authors: Bhajammanavar, Vinod; Mallik, Sumitava; Choutipalli, Venkata Surya Kumar; Subramanian, Venkatesan; Baidya, Mahiuddin
• Is Part Of: Chemical communications. Volume 58:Issue 13(2022)
• Page Start: 2188
• Page End: 2191
• Publication Date: 2022-01-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc06544k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A vinylogy concept driven highly diastereoselective cascade protocol towards [4, 4]-carbospirocycles is developed by leveraging a spiro-annulation reaction through the thermodynamic enolate under organocatalysis. Abstract : A vinylogy concept driven annulation strategy is developed to access [4, 4]-carbospirocycles from alkylidene malononitriles and cyclopentene-1, 3-diones. The reaction is catalyzed by an inexpensive organocatalyst and products with three stereocenters were obtained as a single diastereomer in high yields. The spiro-selectivity originates from the reaction of the thermodynamic enolate intermediate which is fundamentally intriguing.