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Tin(II) Chloride Assisted Synthesis of N-protected γ-amino β-keto Esters Through Semipinacol Rearrangement

Anupam Bandyopadhyay, Neha Agrawal, Sachitanand M Mali, Sandip V Jadhav, Hosahudya N Gopi

Org Biomol Chem. 2010 Nov 7;8(21):4855-60.

PMID: 20734011

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7772998 Tin(II) chloride Tin(II) chloride 7772-99-8 Price
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