Practical synthesis of optically pure menthylamines starting from racemic neomenthol

Synthesis

Volumn , Issue 21, 2010, Pages 3596-3601

  Welschoff, Nina ^a   Waldvogel, Siegfried R ^a,b  

^a UNIVERSITY OF BONN   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

amines; azides; chiral resolution; reduction; terpenoids

Indexed keywords

AZIDES; CHIRAL RESOLUTIONS; NUCLEOPHILIC SUBSTITUTIONS; STARTING MATERIALS; SUBSEQUENT REDUCTION; TARTARIC ACIDS; TECHNICAL PRODUCTS; TERPENOIDS;

ACIDS; LIPIDS;

AMINES;

METHYL AZIDE; METHYLAMINE; METHYLISOTHIOCYANATE; NEOMETHYL METHANESULFONATE; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; DEHYDROGENATION; DIASTEREOISOMER; ENANTIOMER; HYDROGENATION; NUCLEOPHILICITY; RELIABILITY; REPRODUCIBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 77958594284     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258295     Document Type: Article

References (36)

1. Schopohl M C., Siering C, Kataeva O, Waldvogel S R., Angew. Chem. Int. Ed. 2003 42 2620; Angew. Chem. 2003, 115, 2724
2. Siering C, Grimme S, Waldvogel S R., Chem. Eur. J. 2005 11 1877
3. Schopohl M C., Faust A, Mirk D, Fröhlich R, Kataeva O, Waldvogel S R., Eur. J. Org. Chem. 2005 2987
4. Bomkamp M, Siering C, Landrock K, Stephan H, Fröhlich R, Waldvogel S R., Chem. Eur. J. 2007 13 3724
5. Schade W, Bohling C, Hohmann K, Bauer C, Orghici R, Waldvogel S R., Scheel D, Photonic Int. 2007 1 32; Photonik 2006, 38, 70
6. Orghici R, Willer U, Gierszewska M, Waldvogel S R., Schade W, Appl. Phys. B 2008 90 355
7. Börner S, Orghici R, Waldvogel S R., Willer U, Schade W, Appl. Opt. 2009 48 B183
8. Schwartz U, Großer R, Piejko K.-E, Bömer B, Arlt D, German Patent DE3532356A1 1987
9. Chem. Abstr. 1987, 107, 40614
10. Grose-Bley M, Bömer B, Großer R, Arlt D, Lange W, German Patent DE4120695 1992
11. Chem. Abstr. 1993, 119, 139964
12. Bömer B, Großer R, Lange W, Zweering U, Köhler B, Sirges W, Grose-Bley M, DE19546136A1 1997
13. Chem. Abstr. 1997, 127, 96037
14. Lange W, Grosser R, Köhler B, Michel S, Bömer B, Zweering U, DE19714343A1 1998
15. Chem. Abstr. 1998, 129, 290016
16. Looft J, Vössing T, Ley J, Backes M, Blings M, European Patent EP1989944A1 2008
17. Chem. Abstr. 2008, 149, 532086
18. Shimizu T, Ohzeki T, Hiramoto K, Hori N, Nakata T, Synthesis 1999 1373
19. Albrecht S, Defoin A, Tarnus C, Synthesis 2006 1635
20. Nakatsuji H, Ueno K, Misaki T, Tanabe Y, Org. Lett. 2008 10 2131
21. Jumaryatno P, Rands-Trevor K, Blanchfield J T., Garson M J., ARKIVOC 2007 (vii) 157
22. Bartoli G, DiAntonio G, Giovannini R, Giuli S, Lanari S, Paoletti M, Marcantoni E, J. Org. Chem. 2008 73 1919
23. Viaud M C., Rollin P, Synthesis 1990 130
24. Gansuer A, Narayan S, Schiffer-Ndene N, Bluhm H, Oltra J E., Cuerva J M., Rosales A, Nieger M, [nl]J. Organomet. Chem. 2006 691 2327
25. Papeo G, Posteri H, Vianello P, Varasi M, Synthesis 2004 2886
26. Wallach O, Ber. Dtsch. Chem. Ges. 1891 24 3992
27. Wallach O, Kuthe M, Ber. Dtsch. Chem. Ges. 1892 25 3313
28. Wallach O, Kuthe M, Liebigs Ann. Chem. 1893 276 296
29. Kulisch J, Ph.D. Thesis; University of Bonn: Germany 2010
30. Feltkamp H, Kranklin N C., Koch F, Thanh T N., Liebigs Ann. Chem. 1967 707 78
31. Schopohl M C., Bergander K, Kataeva O, Fröhlich R, Waldvogel S R., Synthesis 2003 2689
32. Griesbach U, Waldvogel S R., Kulisch J, Malkowsky I M., Patent WO2008003620 2008
33. Chem. Abstr. 2008, 148, 154171
34. Kuhn W, Funk H U., Senft G, Körber K A., German Patent DE10239274A1 2004
35. Chem. Abstr. 2004, 140, 217823
36. Zuend S J., Jacobsen E N., J. Am. Chem. Soc. 2007 129 15872