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Synthesis 2011(20): 3297-3300  
DOI: 10.1055/s-0030-1260195
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of β-Aminocyclohexanones and β-Aminocyclohexanols through an Intramolecular Tandem Isomerization-Mannich Reaction as a Key Step

Hai Thuong Cao, Danielle Grée, René Grée*
Université de Rennes 1, Laboratoire Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
Fax: +33(2)23236978; e-Mail: rene.gree@univ-rennes1.fr;
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Publication History

Received 29 June 2011
Publication Date:
01 September 2011 (online)

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Abstract

New β-aminocyclohexanones and β-aminocyclohexanols, with a primary amino group, have been obtained by a short and efficient sequence involving an intramolecular tandem isomerization-Mannich reaction as the key step. This methodology takes advantage of tert-butanesulfinyl protection of the nitrogen atom.

Key words

isomerization - catalysis - nickel - carbocycles - Mannich

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