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Synthesis 2010(20): 3410-3414  
DOI: 10.1055/s-0030-1258260
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© Georg Thieme Verlag Stuttgart ˙ New York

Titanium-Catalyzed Cyclopropanation of Boc-Protected Cyanohydrins: A Short Access to Aminocyclopropanecarboxylic Acid Derivatives

Morwenna S. M. Pearson-Longa, Alice Beauseigneura, Philippe Karoyanb, Jan Szymoniakc, Philippe Bertus*a
a CNRS UMR 6011 - Unité de Chimie Organique Moléculaire et Macromoléculaire (UCO2M), Université du Maine, 72085 Le Mans Cedex 09, France
Fax: +33(2)43833902; e-Mail: philippe.bertus@univ-lemans.fr;
b CNRS UMR 7613, Université Pierre-et-Marie Curie Paris 6, 75252 Paris Cedex 05, France
c CNRS UMR 6229, Université de Reims-Champagne Ardenne, BP 1039, 51687 Reims Cedex 2, France
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Publication History

Received 16 June 2010
Publication Date:
17 September 2010 (online)

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Abstract

The preparation of protected 1-aminocyclopropanecarboxylic acid was performed from readily available and inexpensive starting materials, using titanium-catalyzed cyclopropanation as the key step. As an extension of this methodology, a diastereoselective synthesis of the cis-2-vinyl-substituted analogue is presented.

Key words

amino acids - cyanohydrins - cyclopropane - organometallic reagents - titanium

    Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0006th:
  • Primary Data

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14

Respectively ı 400 and ı 300 for 1 g of ACC and Boc-ACC (Aldrich, 2010).

16

The relative configuration of 4c was established by NOESY 2D NMR analysis of the two diastereomers of 5.