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Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza‐Annulation Reactions
Author(s) -
Hayrapetyan Davit,
Stepanova Valeriya
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100255
Subject(s) - annulation , chemistry , stereocenter , moiety , stereochemistry , beta lactam , combinatorial chemistry , lactam , double bond , organic chemistry , enantioselective synthesis , catalysis , biochemistry , antibiotics
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.