Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions


Hayrapetyan D. Stepanova V.
15 April 2021John Wiley and Sons Inc

European Journal of Organic Chemistry
2021#2021Issue 142121 - 2125 pp.

Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the exocyclic C=C double bond of the enamide moiety proceeded with excellent diastereoselectivity. Overall, one C−C and two C−N bonds, as well as three new stereocenters were created in a diastereoselective manner resulting in a fast upbuild of molecular complexity.

Annulation , Diastereoselectivity , Lactams , Nitrogen heterocycles , Spiro compounds

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Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave., Nur-Sultan, 010000, Kazakhstan

Department of Chemistry

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