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Issue 27, 2012

Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

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Abstract

Michael addition reaction of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give β-formyl-β′-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl β-nitroacrylates as Michael acceptors, the obtained β-formyl-β′-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin®) in one step from the Michael adducts in high yields.

Graphical abstract: Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

Supplementary files

Article information


Submitted
25 Feb 2012
Accepted
16 May 2012
First published
16 May 2012

Org. Biomol. Chem., 2012,10, 5289-5297
Article type
Paper

Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

M. Yoshida, E. Masaki, H. Ikehara and S. Hara, Org. Biomol. Chem., 2012, 10, 5289 DOI: 10.1039/C2OB25413A

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