Copper catalysed asymmetric ring opening reaction of oxabenzonorbornadienes with grignard and aluminium reaggents

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Title		Copper catalysed asymmetric ring opening reaction of oxabenzonorbornadienes with grignard and aluminium reaggents
Authors		Millet, Renaud Gremaud, Ludovic Bernardez, Tania Palais, Laetitia Alexakis, Alexandre
Published in		Synthesis. 2009, no. 12, p. 2101-2112
Abstract		A highly enantioselective method for the copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand has been developed. The same reaction with Grignard reagents is also reported. A wide range of alkyl chains have been used with moderate to high enantioselectivity and high trans selectivity. The transfer of a methyl group is also reported with high enantiomeric and diastereomeric excess and yields for different substrates. We finally have been able to perform the first trans enantioselective desymmetrization of oxabenzonorbornadienes with an aromatic group.
Keywords		Copper catalysis — Asymmetric transformation — Grignard reagents — Aluminum reagents — SimplePhos
Identifiers		DOI: 10.1055/s-0029-1216838
Full text		Article (Published version) - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Citation (ISO format)		MILLET, Renaud et al. Copper catalysed asymmetric ring opening reaction of oxabenzonorbornadienes with grignard and aluminium reaggents. In: Synthesis, 2009, n° 12, p. 2101-2112. https://archive-ouverte.unige.ch/unige:8238

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Deposited on : 2010-06-21

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