2026-10-14T04:45:35Z https://api.figshare.com/v2/oai

oai:figshare.com:article/33917078 2026-09-18T02:03:48Z category_4 category_7 category_8 category_24 category_873 category_46 category_132 category_135 portal_63 item_type_3 month_year_09_2026

Enantioselective Synthesis of Spiropyrrolidines by Synergistic Catalysis Michael Franc (19965025) Ivana Císařová (1580947) Jan Veselý (1843195) Biochemistry Medicine Microbiology Evolutionary Biology Chemical Sciences not elsewhere classified Immunology Infectious Diseases Computational Biology good combined yields enantioselectivities reaching 99 optimized reaction conditions achiral palladium catalysis reaction partners work highlights synergistic catalysis stereoselective methodology metal catalysis high diastereoselectivities enantiomeric purity efficient construction broad range aldimines derived activated vinylcyclopropanes 83 %), 12 dr A stereoselective methodology for the synthesis of highly substituted spiropyrrolidines via synergistic catalysis was developed. The transformation is based on a cooperative catalytic system combining chiral phosphoric acid (CPA) catalysis with achiral palladium catalysis and proceeds through a formal [3+2] cycloaddition of activated vinylcyclopropanes with aldimines derived from imidazolones. Under the optimized reaction conditions, a broad range of spiropyrrolidines were obtained in good combined yields (up to 83%), with high diastereoselectivities (up to 1:12 dr) and enantioselectivities reaching 99% ee. The developed methodology tolerates various substitutions on both of the reaction partners. Furthermore, selected synthetic transformations demonstrated the utility of the obtained spiropyrrolidines for further derivatization while retaining the enantiomeric purity. This work highlights the potential of synergistic CPA/transition-metal catalysis for the efficient construction of structurally complex chiral spiropyrrolidine scaffolds. 2026-09-17T00:00:00Z Dataset Dataset 10.1021/acs.joc.6c01686.s002 https://figshare.com/articles/dataset/Enantioselective_Synthesis_of_Spiropyrrolidines_by_Synergistic_Catalysis/33917078 CC BY-NC 4.0