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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
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Article (Published version) - document accessible for UNIGE members only 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. doi: 10.1055/s-0029-1216838 https://archive-ouverte.unige.ch/unige:8238

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Deposited on : 2010-06-21

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