Tin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement

A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction i...

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Veröffentlicht in:Organic & biomolecular chemistry 2010-11, Vol.8 (21), p.4855-4860
Hauptverfasser: Bandyopadhyay, Anupam, Agrawal, Neha, Mali, Sachitanand M, Jadhav, Sandip V, Gopi, Hosahudya N
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Sprache:eng
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Zusammenfassung:A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00199f