Synthesis and Characterization of Enantiomerically Pure Menthylamines and Their Isocyanates

Matthias C. Schopohl; Klaus Bergander; Olga Kataeva; Roland Fröhlich; Siegfried R. Waldvogel

doi:10.1055/s-2003-42432

PAPER

Synthesis and Characterization of Enantiomerically Pure Menthylamines and Their Isocyanates

Matthias C. Schopohl^a, Klaus Bergander^a, Olga Kataeva^b, Roland Fröhlich^a, Siegfried R. Waldvogel*^a
^a Westfälische Wilhelms-Universität Münster, Org.-Chem. Institut, Corrensstr. 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: waldvog@uni-muenster.de;
^b H. E. Arbuzov Institute, Arbuzov Street 8, Kazan 420088, Russia

Abstract

Alle Artikel dieser Rubrik

Abstract

A synthetic protocol for optically pure (-)-menthylamine, (-)-8-methylmenthylamine, and the novel (-)-8-phenylmenthylamine is presented including a detailed characterization of these compounds and their isocyanates.

Key words

amines - aminations - asymmetric synthesis - chirality - chiral auxiliaries

Volltext

Referenzen

References

<A NAME="RT08303SS-1">1</A> Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis Wiley Inter-Science; New York: 1995. p.57-58

<A NAME="RT08303SS-2A">2a</A> James BR. Catal. Today 1997, 37: 209

<A NAME="RT08303SS-2B">2b</A> Denmark SE. Nicaise OJ.-C. Chem. Commun. 1996, 999

<A NAME="RT08303SS-2C">2c</A> Beak P. Zajdel WJ. Reitz DB. Chem. Rev. 1984, 84: 471

<A NAME="RT08303SS-2D">2d</A> Ellman JA. Pure Appl. Chem. 2003, 75: 39

<A NAME="RT08303SS-3">3</A> Zhou P. Chen B. Davis FA. In Advances in Sulfur Chemistry Vol. 2: JAI Press; New York: 2000. p.249-282 ; and literature cited therein

<A NAME="RT08303SS-4">4</A> Schopohl MC. Siering C. Kataeva O. Waldvogel SR. Angew. Chem. Int. Ed. 2003, 42: 2620

<A NAME="RT08303SS-5A">5a</A> Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650

<A NAME="RT08303SS-5B">5b</A> Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis GE. Angew. Chem. Int. Ed. 2002, 41: 1668

<A NAME="RT08303SS-6">6</A> Hueckel W. Sommer W. Liebigs Ann. Chem. 1965, 687: 102

<A NAME="RT08303SS-7A">7a</A> Feltkamp H. Koch F. Thanh TN. Liebigs Ann. Chem. 1967, 707: 78

<A NAME="RT08303SS-7B">7b</A> Cope AC. Acton EM. J. Am. Chem. Soc. 1958, 80: 355

<A NAME="RT08303SS-8A">8a</A> Ort O. Org. Synth. 1987, 65: 203

<A NAME="RT08303SS-8B">8b</A> Fernández F. García-Mera X. López C. Rodríguez-Borges JE. Tetrahedron: Asymmetry 2000, 11: 4805

<A NAME="RT08303SS-8C">8c</A> Flemming S. Kabbara J. Nickisch K. Neh H. Westermann J. Synthesis 1995, 317

<A NAME="RT08303SS-8D">8d</A> Costello DP. Geraghty NWA. Synth. Commun. 1999, 29: 3083

<A NAME="RT08303SS-9A">9a</A> Eck JC. Marvel CS. Org. Synth., Coll. Vol. 2 Wiley; London: 1943. p.76

<A NAME="RT08303SS-9B">9b</A> Bousquet EW. Org. Synth., Coll. Vol. 2 Wiley; London: 1943. p.314

Despite the analytical purity and different ways to produce the crystalline material, our melting point was 35 °C below the reported datum in the reference. [6]

The stereochemical assignment refers to the systematic numbering of the menthane skeleton and corresponds to (1R,2S,5R)-cyclohexylamine.

<A NAME="RT08303SS-12">12</A> Otwinowski Z. Minor W. Methods in Enzymology 1997, 276: 307

<A NAME="RT08303SS-13A">13a</A> Blessing RH. Acta Cryst. 1995, A51: 33

<A NAME="RT08303SS-13B">13b</A> Blessing RH. J. Appl. Cryst. 1997, 30: 421

<A NAME="RT08303SS-14">14</A> Sheldrick GM. Acta Cryst. 1990, A46: 467