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

Morwenna S. M. Pearson-Long; Alice Beauseigneur; Philippe Karoyan; Jan Szymoniak; Philippe Bertus

doi:10.1055/s-0030-1258260

PSP

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

Morwenna S. M. Pearson-Long^a, Alice Beauseigneur^a, Philippe Karoyan^b, Jan Szymoniak^c, 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

Abstract

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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

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References

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16

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

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