Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines.

Autor: Jessen NI; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Bura M; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Bertuzzi G; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Jørgensen KA; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Aug 16; Vol. 60 (34), pp. 18527-18531. Date of Electronic Publication: 2021 Jul 19.
DOI: 10.1002/anie.202106287
Abstrakt: An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.
(© 2021 Wiley-VCH GmbH.)
Databáze: MEDLINE
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