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Synthesis 2004(13): 2222-2225
DOI: 10.1055/s-2004-829180
DOI: 10.1055/s-2004-829180
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
1-Aza-2-siloxybutadiene: Structure and Synthetic Application as a Piperidinone Synthon
Further Information
Received
21 May 2004
Publication Date:
30 July 2004 (online)
Publication History
Publication Date:
30 July 2004 (online)
Abstract
Synthesis of 1-aza-2-siloxydienes and their structural analysis by multinuclear NMR are described. Moreover, the cycloaddition reaction of the isolated 1-aza-2-siloxydienes with dienophiles to synthesize piperidin-2-ones was explored.
Key words
silicon - amides - piperidines - cycloadditions - tandem reactions
-
1a
Carruthers W. Cycloaddition Reactions in Organic Synthesis Pergamon Press; Oxford: 1990. -
1b
Cycloaddition Reactions in Organic Synthesis
Kobayashi S.Jørgensen KA. Wiley-VCH; Weinheim: 2002. -
2a
Boger DL.Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis Academic Press; San Diego: 1987. -
2b
Jayakumar S.Ishar MPS.Mahajan MP. Tetrahedron 2002, 58: 379 - Synthesis of piperidines by intermolecular cyclodimerization of acrylamide equivalents:
-
3a
Lorente A.Navio JLG.Perez JCL.Soto JL. Synthesis 1985, 89 -
3b
Elliott MC.Galea NM.Long MS.Willock DJ. Tetrahedron Lett. 2001, 42: 4937 - Synthesis of piperidines by intramolecular cycloaddition of α,β-unsaturated amides:
-
4a
Ihara M.Ishida Y.Tokunaga Y.Kabuto C.Fukumoto K. J. Chem. Soc., Chem. Commun. 1995, 2085 -
4b
Toyota M.Komori C.Ihara M. J. Org. Chem. 2000, 65: 7110 -
4c
Mekouar K.Genisson Y.Leue S.Greene AE. J. Org. Chem. 2000, 65: 5212 - 5
Takasu K.Nishida N.Ihara M. Tetrahedron Lett. 2003, 44: 7429 - 6
Jones K.Wilkinson J.Ewin R. Tetrahedron Lett. 1994, 35: 7673 - For comparable examples, structural analysis of silylated benzamides:
-
7a
Klebe JF. Acc. Chem. Res. 1970, 3: 299 -
7b
Misaki T.Kurihara M.Tanabe Y. Chem. Commun. 2001, 2478 - 8
Levy GC.Lichter RL. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy John Wiley & Sons; New York: 1979. - 9
Jancke H.Engelhardt G.Wagner S.Dirnens W.Herzog G.Tieme E.Rühlmann K. J. Organomet. Chem. 1977, 134: 21