New Lewis-Basic N-Oxides as Chiral Organocatalysts in Asymmetric Allylation of Aldehydes
The Journal of Organic Chemistry2003Vol. 68(25), pp. 9659–9668
Citations Over TimeTop 10% of 2003 papers
Andrei V. Malkov, Mark Bell, Monica Orsini, Daniele Pernazza, António Massa, Pavel Herrmann, Premji Meghani, Pavel Kočovský
Abstract
Allylation of aromatic and heteroaromatic aldehydes 1a-k with allyltrichlorosilane 2 can be catalyzed by the new heterobidentate, terpene-derived bipyridine N-monoxides 4, 6a,b, and 8-11 (</=10 mol %) to afford (S)-(-)-3 with high enantioselectivities (</=99% ee). The stereochemical outcome has been found to be controlled by the axial chirality of the catalyst, which in turn is determined by the central chirality of the annulated terpene units. Solvent effects on the conversion and the level of asymmetric induction have been elucidated, and MeCN has been identified as the optimal solvent for these catalysts.
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