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

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Synthesis 2003(17): 2689-2694
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

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Publication History

Received 31 July 2003
Publication Date:
14 October 2003 (online)

Abstract
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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

References

1 Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis Wiley Inter-Science; New York: 1995. p.57-58

Google Scholar
2a James BR. Catal. Today 1997, 37: 209

Crossref Google Scholar
2b Denmark SE. Nicaise OJ.-C. Chem. Commun. 1996, 999

Crossref Google Scholar
2c Beak P. Zajdel WJ. Reitz DB. Chem. Rev. 1984, 84: 471

Crossref Google Scholar
2d Ellman JA. Pure Appl. Chem. 2003, 75: 39

Crossref Google Scholar
3 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

Google Scholar
4 Schopohl MC. Siering C. Kataeva O. Waldvogel SR. Angew. Chem. Int. Ed. 2003, 42: 2620

Crossref Google Scholar
5a Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650

Crossref PubMed Google Scholar
5b Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis GE. Angew. Chem. Int. Ed. 2002, 41: 1668

Crossref PubMed Google Scholar
6 Hueckel W. Sommer W. Liebigs Ann. Chem. 1965, 687: 102

Crossref Google Scholar
7a Feltkamp H. Koch F. Thanh TN. Liebigs Ann. Chem. 1967, 707: 78

Crossref Google Scholar
7b Cope AC. Acton EM. J. Am. Chem. Soc. 1958, 80: 355

Crossref Google Scholar
8a Ort O. Org. Synth. 1987, 65: 203

Crossref Google Scholar
8b Fernández F. García-Mera X. López C. Rodríguez-Borges JE. Tetrahedron: Asymmetry 2000, 11: 4805

Crossref Google Scholar
8c Flemming S. Kabbara J. Nickisch K. Neh H. Westermann J. Synthesis 1995, 317

Crossref Google Scholar
8d Costello DP. Geraghty NWA. Synth. Commun. 1999, 29: 3083

Crossref Google Scholar
9a Eck JC. Marvel CS. Org. Synth., Coll. Vol. 2 Wiley; London: 1943. p.76

Google Scholar
9b Bousquet EW. Org. Synth., Coll. Vol. 2 Wiley; London: 1943. p.314

Google Scholar
12 Otwinowski Z. Minor W. Methods in Enzymology 1997, 276: 307

PubMed Google Scholar
13a Blessing RH. Acta Cryst. 1995, A51: 33

Crossref Google Scholar
13b Blessing RH. J. Appl. Cryst. 1997, 30: 421

Crossref Google Scholar
14 Sheldrick GM. Acta Cryst. 1990, A46: 467

Crossref Google Scholar

10

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]

11

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