Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides: A Possible Intermediate Characterized
Organic Letters2009Vol. 11(9), pp. 1907–1910
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Baptiste Lecachey, Nicolas Duguet, Hassan Oulyadi, Catherine Fressigné, Anne Harrison‐Marchand, Yasutomo Yamamoto, Kiyoshi Tomioka, Jacques Maddaluno
Abstract
Two 1:1 noncovalent mixed aggregates between a lithium enolate and two diastereomeric lithium amides have been identified spectroscopically in THF. The NMR data, as well as DFT theoretical calculations, shine some light on a puzzling reversal of induction, observed when switching from one diastereomer of the amide to the other in the enantioselective Michael addition of the lithium enolate to an unsaturated ester.
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