Organocatalytic asymmetric ring-opening of aziridines.
نویسندگان
چکیده
The organocatalytic ring-opening of N-tosyl protected aziridines by beta-ketoesters under chiral PTC-conditions, leading to the formation of optically active aminoethyl functionalised compounds with up to 99% ee, has been developed.
منابع مشابه
The organocatalytic ring-opening polymerization of N-tosyl aziridines by an N-heterocyclic carbene.
The ring-opening polymerization of N-tosyl aziridines, in the presence of 1,3-bis(isopropyl)-4,5(dimethyl)imidazol-2-ylidene as an organocatalyst and an N-tosyl secondary amine as initiator mimicking the growing chain, provides the first metal-free route to well defined poly(aziridine)s (PAz) and related PAz-based block copolymers.
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A new method for asymmetric ring opening of terminal aziridines using a chiral amine, (DHQD)(2)AQN, is described; the reaction is based on the asymmetric recognition of aziridines using (DHQD)(2)AQN and on sequential ring opening using TMSNu.
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The asymmetric ring-opening of meso-aziridines with primary alcohols is realized using an N,N'-dioxide-Mg(OTf)2 complex as the catalyst. The desired vicinal trans-β-amino ethers are afforded in good yields and enantioselectivities. Aniline and water could also be used as the nucleophiles for the ring-opening in an identical catalyst system.
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An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for ph...
متن کاملMetal-free borylative ring-opening of vinyl epoxides and aziridines.
A rational approach towards the borylative ring-opening of vinylepoxides and vinylaziridines, by the in situ formed MeO(-)→bis(pinacolato)diboron adduct, has been developed. The enhanced nucleophilic character of the Bpin (sp(2)) moiety from the reagent favours the SN2' conjugated B addition with the concomitant opening of the epoxide and aziridine rings. The reaction proceeds with total chemos...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 6 19 شماره
صفحات -
تاریخ انتشار 2008