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ß- and γ- disubstituted olefins: susbtrates for copper-catalysed asymmetric allylic substitution

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Published in Advanced Synthesis and Catalysis. 2008, vol. 350, no. 7-8, p. 1090-1100
Abstract The copper-catalyzed asymmetric allylic alkylation has shown through many examples that it is a powerful means to generate stereogenic centers with mono - and -substituted olefinic substrates. However, little has been reported about more substituted olefinic patterns, such as -disubstituted allylic electrophiles. In this paper, we show that a simple procedure using easily accessible Grignard reagents and as low as 3 mol% of copper/ligand can promote high to nearly perfect enantioselectivities (up to >99% ee) with very good -selectivities on a wide panel of aliphatic or aromatic -disubstituted substrates.
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FALCIOLA, Caroline Alexandra et al. ß- and γ- disubstituted olefins: susbtrates for copper-catalysed asymmetric allylic substitution. In: Advanced Synthesis and Catalysis, 2008, vol. 350, n° 7-8, p. 1090-1100. https://archive-ouverte.unige.ch/unige:8100

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Deposited on : 2010-06-21

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