Synthesis of Substituted Piperidines, Decahydroquinolines and Octahydroindolizines by Radical Rearrangement Reactions of 2-Alkylideneaziridines

Autor:	Natacha Prevost, Michael Shipman
Rok vydání:	2003
Předmět:	Chemistry Radical Organic Chemistry Drug Discovery Organic chemistry General Medicine Biochemistry Medicinal chemistry Bond cleavage
Zdroj:	ChemInform. 34
ISSN:	1522-2667 0931-7597
Popis:	Rearrangement of a variety of 3-(2-methyleneaziridin-1-yl)propyl radicals, generated using Bu 3 SnH/AIBN by homolytic cleavage of phenylselenide substituted 2-methyleneaziridines, produces 3-methylenepiperidines in yields ranging from 58 to 68%. By combining this radical rearrangement with an additional 5- exo -trig cyclisation, this method provides an octahydroindolizine with moderate levels of diastereocontrol (d.r.=4:1). This rearrangement works with related 2-isopropylideneaziridines, but cannot be successfully extended to 4-(2-methyleneaziridin-1-yl)butyl radicals.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f9310d4c2e42fb3d48a586b8300795c4 https://doi.org/10.1002/chin.200306043 Zobrazit plný text záznamu Plný text