RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(8): 1334-1338
DOI: 10.1055/s-0029-1218672
DOI: 10.1055/s-0029-1218672
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Straightforward Access to α-Methylamines through Cross-Metathesis
Weitere Informationen
Received
15 December 2009
Publikationsdatum:
05. Februar 2010 (online)
Publikationsverlauf
Publikationsdatum:
05. Februar 2010 (online)

Abstract
A two-step procedure involving cross-metathesis and reductive amination enables easy access to α-methylamines and α,α′-dimethyldiamines from a wide variety of terminal olefins.
Key words
amines - alkenes - metathesis - ruthenium - hydrogenation
- 1
Lawrence SA. Amines: Synthesis, Properties and Applications Cambridge University Press; Cambridge: 2004. -
2a
Nechab M.Azzi N.Vanthuyne N.Bertrand MP.Gastaldi S.Gil G. J. Org. Chem. 2007, 72: 6918 -
2b
El Blidi L.Nechab M.Vanthuyne N.Gastaldi S.Bertrand MP.Gil G. Org. Biomol. Chem. 2008, 6: 3917 - 3
Routaboul L.Vanthuyne N.Gastaldi S.Gil G.Bertrand MP. J. Org. Chem. 2008, 73: 364 - 4
Gastaldi S.Escoubet S.Vanthuyne N.Gil G.Bertrand MP. Org. Lett. 2007, 9: 837 - 5
El Blidi L.Nechab M.Vanthuyne N.Gastaldi S.Gil G.Bertrand MP. J. Org. Chem. 2009, 74: 2901 - 6
van Rantwijk F.Sheldon RA. Tetrahedron 2004, 60: 501 ; and references cited therein - 7
Bornscheuer UT.Kazlauskas RJ. Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations 2nd ed.: Wiley-VCH; Weinheim: 2006. Chap. 6 and references cited therein - 8 For a review on the synthesis of α-branched
chiral amines, see:
Bräse S.Baumann T.Dahmen S.Vogt H. Chem. Commun. 2007, 1881 - For a review, see:
-
9a
Gomez S.Peters JA.Maschmeyer T. Adv. Synth. Catal. 2002, 344: 1037 -
9b
Tararov VI.Börner A. Synlett 2005, 203 -
9c
Tripathi RP.Verma SS.Pandey J.Tiwari VK. Curr. Org. Chem. 2008, 12: 1093 - 10 For a review, see:
Ferraris D. Tetrahedron 2007, 63: 9581 - 11 For a review, see:
Barrett AGM.Graboski GG. Chem. Rev. 1986, 86: 751 - 12 For a review dealing with olefin
cross-metathesis, see:
Connon SJ.Blechert S. Angew. Chem. Int. Ed. 2003, 42: 1900 - 13
Michaut A.Boddaert T.Coquerel Y.Rodriguez J. Synthesis 2007, 2867 - 14
Gessler S.Randl S.Blechert S. Tetrahedron Lett. 2000, 41: 9973 - 15
Monfette S.Fogg DE. Chem. Rev. 2009, 109: 3783 - For selected examples of ring-opening cross-metathesis, see:
-
16a
Roe SJ.Legeay J.-C.Robbins D.Aggarwal P.Stockman RA. Chem. Commun. 2009, 4399 -
16b
Randl S.Connon SJ.Blechert S. Chem. Commun. 2001, 1796 -
16c
Morgan JP.Morrill C.Grubbs RH. Org. Lett. 2002, 4: 67 - 17
Veld MAJ.Hult K.Palmans ARA.Meijer EW. Eur. J. Org. Chem. 2007, 5416 - 18
Crandall JK.Pradat C. J. Org. Chem. 1985, 50: 1327 - 19
Lanners S.Norouzi-Arasi H.Khiri N.Hanquet G. Eur. J. Org. Chem. 2007, 4065