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Solvent-free organocatalytic Michael addition of diethyl malonate to nitroalkenes: the practical synthesis of Pregabalin and γ-nitrobutyric acid derivatives by Jin-ming Liu; Xin Wang; Ze-mei Ge; Qi Sun; Tie-ming Cheng; Run-tao Li is a Chemistry article available to read on EtoBox.

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A highly enantioselective synthesis of Pregabalin 1 hydrochloride with good overall yield (44%) and enantioselectivity (98% ee) was described. The key step is an asymmetric Michael addition of equivalent of diethyl malonate and nitroalkene under solvent-free conditions using thiourea 2 as catalyst. The reaction can be applied to a variety of aromatic and aliphatic substituted nitroalkenes affording corresponding adducts in good to excellent yields (61e92%) and enantioselectivities (78e93% ee).

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Author

Jin-ming Liu; Xin Wang; Ze-mei Ge; Qi Sun; Tie-ming Cheng; Run-tao Li

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2011

Language

EN

Field

Chemistry (Physical Sciences)