Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines

Autor:	Ana Teresa Carmona Asenjo, Inmaculada Robina, Pilar Elías-Rodríguez, Antonio José Moreno Vargas
Rok vydání:	2022
Předmět:	[3 + 2]-cycloaddition allenes pyrrolidines phosphines organocatalysis Physical and Theoretical Chemistry Catalysis General Environmental Science
Zdroj:	Catalysts; Volume 12; Issue 8; Pages: 876
ISSN:	2073-4344
Popis:	Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The stereochemical outcome of the reaction depends on the substituent at the nitrogen atom and hydroxyl groups, the configuration of the stereogenic centers and the distance between the diphenylphosphine group and the pyrrolidine skeleton of the catalyst. The preparation of both enantiomers of the catalyst allowed the corresponding enantiomeric pyrrolines to be obtained with similar yields, diastereo- and enantioselectivities.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::72f09621b7c38bcc9fd01413ca913a60 https://doi.org/10.3390/catal12080876 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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