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

Organic & biomolecular chemistry (2010-08-25)
Anupam Bandyopadhyay, Neha Agrawal, Sachitanand M Mali, Sandip V Jadhav, Hosahudya N Gopi
RESUMEN

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.

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Sigma-Aldrich
Tin(II) chloride dihydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥98%