Isothiourea-catalysed enantioselective synthesis of phosphonate-functionalised β-lactones.

• Tác giả: David B Cordes, Aidan P McKay, Heena Panchal, Ffion M Platt, Alexandra M Z Slawin, Andrew D Smith, Yihong Wang
• Ngôn ngữ: eng
• Ký hiệu phân loại: 181.119 *Korea
• Thông tin xuất bản: England : Chemical science , 2025
• Bộ sưu tập: NCBI
• ID: 725413
• Chủ đề: 1. Coastal Biological Diversity Coastal Zone Biodiversity Diversity, Coastal Biological

Tóm tắt

Despite growing interest in the reactivity and biological activity of phosphonate-containing molecules, the application of α-ketophosphonates in enantioselective formal [2 + 2] cycloadditions to generate β-lactones bearing a pendant phosphonate group remains unreported. In this manuscript, a highly diastereo- and enantioselective isothiourea-catalysed formal [2 + 2] cycloaddition of both alkyl- and aryl substituted C(1)-ammonium enolates and α-ketophosphonates is established. This strategy allows a mild, practical and scalable approach to highly enantioenriched C(3)-unsubstituted and C(3)-alkyl β-lactones bearing a phosphonate motif from their corresponding α-silyl acids,