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

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
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tin(II) chloride dihydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥98%
Sigma-Aldrich
Ethyl diazoacetate, contains ≥13 wt. % dichloromethane