Molecules
(Oct 2022)
Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
Anna N. Philippova,
Daria V. Vorobyeva,
Pavel S. Gribanov,
Fedor M. Dolgushin,
Sergey N. Osipov
Affiliations
Anna N. Philippova
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28/1, 119334 Moscow, Russia
Daria V. Vorobyeva
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28/1, 119334 Moscow, Russia
Pavel S. Gribanov
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28/1, 119334 Moscow, Russia
Fedor M. Dolgushin
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Prosp., 119071 Moscow, Russia
Sergey N. Osipov
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28/1, 119334 Moscow, Russia
DOI
https://doi.org/10.3390/molecules27206898
Journal volume & issue
Vol. 27,
no. 20
Abstract
Read online
An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.
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