Synthesis of Polyhydroxylated Pyrrolidines and Aziridinopyrrolidines from [4π+2π] Cycloadducts of Cyclopentadiene and Imines/2H-Azirines

Autor:	Maria J. Alves, Marı́a Luisa C. Vale, Fabio Rizzo Aguiar, Xerardo García-Mera, José E. Rodríguez-Borges
Rok vydání:	2008
Předmět:	chemistry.chemical_compound Sodium borohydride Cyclopentadiene chemistry Osmium tetroxide Sodium periodate Dihydroxylation Organic Chemistry Enantioselective synthesis Organic chemistry Hydroxymethyl Aziridine Catalysis
Zdroj:	Synthesis. 2008:971-977
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2008-1032196
Popis:	The synthesis of 2-functionalized 3,5-bis(hydroxymethyl)pyrrolidines from readily available polycyclic Diels-Alder adducts by a reaction sequence involving three steps is described. The same methodology has been applied to obtain the aziridine counterparts from the corresponding methyl 2-azatricyclo[3.2.1.0 2,4 ]oct-6-ene-4-carboxylates. The key steps in the synthetic strategy are dihydroxylation with osmium tetroxide/ N-methylmorpholine N-oxide, oxidative cleavage with sodium periodate, and reduction using sodium borohydride or lithium aluminum hydride; overall yields ranged from 40-60%.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::04c9e9bb606f99304314ff8d8a675887 https://doi.org/10.1055/s-2008-1032196 Zobrazit plný text záznamu