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Synthesis 2010(21): 3596-3601
DOI: 10.1055/s-0030-1258295
DOI: 10.1055/s-0030-1258295
PSP
© Georg Thieme Verlag
Stuttgart ˙ New YorkPractical Synthesis of Optically Pure Menthylamines Starting from Racemic Neomenthol
Weitere Informationen
Received
20 August 2010
Publikationsdatum:
13. Oktober 2010 (online)
Publikationsverlauf
Publikationsdatum:
13. Oktober 2010 (online)
Abstract
A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.
Key words
amines - azides - chiral resolution - reduction - terpenoids
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