Abstract
Several new cyclopropylisonitriles were synthesized from the corresponding cyclopropylamines (41-69% yield) and utilized in Ugi four-component reactions to furnish 12 new dipeptides in 38-86% yield. The structures of four of these dipeptides were determined by X-ray crystallography.
Key words
ring constructions - titanium chemistry - multicomponent reactions - dipeptides - isonitriles
References
1b Zhao L.
de Meijere A.
Adv. Synth. Catal.
2006,
348:
in press
1a von Seebach M.
Kozhushkov SI.
Frank D.
Boese R.
Benet-Buchholz J.
Yufit DS.
Schill H.
de Meijere A.
Chem. Eur. J.
2007,
13: Early View; DOI: 10.1002/chem.200600799
2 Dömling A.
Ugi I.
Angew. Chem. Int. Ed.
2000,
39:
3168
3 Kulinkovich OG.
de Meijere A.
Chem. Rev.
2000,
100:
2789
4a de Meijere A.
Kozhushkov SI.
Savchenko AI.
Titanium and Zirconium in Organic Synthesis
Marek I.
Wiley-VCH;
Weinheim:
2002.
p.390
4b de Meijere A.
Kozhushkov SI.
Savchenko AI.
J. Organomet. Chem.
2004,
689:
2033
5a Gensini M.
Kozhushkov SI.
Yufit DS.
Howard JAK.
Es-Sayed M.
de Meijere A.
Eur. J. Org. Chem.
2002,
2499
5b Laroche C.
Behr J.-B.
Szymoniak J.
Bertus P.
Plantier-Royon R.
Eur. J. Org. Chem.
2005,
5084 ; and references cited therein
6 de Meijere A.
Williams CM.
Kourdioukov A.
Sviridov SV.
Chaplinski V.
Kordes M.
Savchenko AI.
Stratmann C.
Noltemeyer M.
Chem. Eur. J.
2002,
8:
3789
7 Obrecht R.
Herrmann R.
Ugi I.
Synthesis
1985,
400
8 Schöllkopf U.
Hoppe D.
Jentsch R.
Angew. Chem.
1971,
83:
357
9 Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited as supplementary publication no. CCDC 604790 (15b ), CCDC 604791 (15d ), CCDC 604792 (15h ), CCDC 604703 (15i ) with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.
