Issue 29, 2017
From the journal:

Organic & Biomolecular Chemistry

Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones†

Feng Yin,a   Ainash Garifullinaa  and  Fujie Tanaka ORCID logo *a  

* Corresponding authors

a Chemistry and Chemical Bioengineering Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna, Okinawa 904-0495, Japan
E-mail: ftanaka@oist.jp

Abstract

To concisely synthesize highly enantiomerically enriched 5-alkyl-substituted pyrrolidine-3-carboxylic acids, organocatalytic enantioselective Michael addition reactions of 4-alkyl-substituted 4-oxo-2-enoates with nitroalkanes have been developed. Using the developed reaction method, 5-methylpyrrolidine-3-carboxylic acid with 97% ee was obtained in two steps.

Graphical abstract: Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

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Article information

DOI
https://doi.org/10.1039/C7OB01484H
Article type
Communication
Submitted
20 Jun 2017
Accepted
30 Jun 2017
First published
30 Jun 2017

Org. Biomol. Chem., 2017,15, 6089-6092

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Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

F. Yin, A. Garifullina and F. Tanaka, Org. Biomol. Chem., 2017, 15, 6089 DOI: 10.1039/C7OB01484H

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