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Updated: Aug 29, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
New Lewis-basic N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes
Andrei V Malkov1, Mark Bell, Monica Orsini
1Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K.
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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