Enantioselective Synthesis of Spiropyrrolidines by Synergistic Catalysis.
- 1Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43Praha 2, Czech Republic.
- 2Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43Praha 2, Czech Republic.
Abstract
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.
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BibTeX
@article{franc2026enantioselective,
title = {{Enantioselective Synthesis of Spiropyrrolidines by Synergistic Catalysis.}},
author = {Michael Franc and Ivana Císařová and Jan Veselý},
journal = {The Journal of organic chemistry},
year = {2026},
month = oct,
doi = {10.1021/acs.joc.6c01686},
url = {https://europepmc.org/article/MED/42916954},
note = {CC BY},
}
RIS
TY - JOUR
TI - Enantioselective Synthesis of Spiropyrrolidines by Synergistic Catalysis.
AU - Michael Franc
AU - Ivana Císařová
AU - Jan Veselý
PY - 2026
DA - 2026/10/01
JO - The Journal of organic chemistry
DO - 10.1021/acs.joc.6c01686
UR - https://europepmc.org/article/MED/42916954
AB - 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.
SN - 0022-3263
SN - 1520-6904
ER -