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Synthesis 2004(7): 1041-1046  
DOI: 10.1055/s-2004-822335
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Synthesis of Optically Pure α-Branched Aliphatic Carboxylic Acids from Amidines

Flavio Cassani, Giuseppe Celentano, Emanuela Erba*, Donato Pocar
Istituto di Chimica Organica ‘Alessandro Marchesini’ e Centro Interuniversitario di Ricerca sulle Reazioni Pericicliche e Sintesi di Sistemi Etero-e Carbociclici, Università degli Studi di Milano, Via G. Venezian, 21, 20133 Milano, Italy
Fax: +39(02)50314476; e-Mail: emanuela.erba@unimi.it;
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Publication History

Received 16 February 2004
Publication Date:
14 April 2004 (online)

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Abstract

A range of amidines containing amino acid function was easily prepared in good yields from simple starting materials. Starting from l- or d- proline and linear symmetric ketones, optically pure amidines were prepared. Hydrolysis of these amidines afforded optically pure branched aliphatic carboxylic acids.

Key words

amidine - aliphatic carboxylic acid - valproic acid (2-propylpentanoic acid) - circular dichroism

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