Synlett 2015; 26(06): 807-809
DOI: 10.1055/s-0034-1379999
letter
© Georg Thieme Verlag Stuttgart · New York

Disulfonimide-Catalyzed Asymmetric Synthesis of δ-Amino-β-Keto Esters

Qinggang Wang
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   eMail: list@mpi-muelheim.mpg.de
,
Benjamin List*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   eMail: list@mpi-muelheim.mpg.de
› Institutsangaben
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Publikationsverlauf

Received: 02. Dezember 2014

Accepted after revision: 12. Januar 2015

Publikationsdatum:
10. Februar 2015 (online)


Abstract

A chiral disulfonimide-catalyzed asymmetric synthesis of δ-amino-β-keto esters via a vinylogous Mukaiyama–Mannich reaction of the Chan diene with N-Boc imines has been developed. The desired products were obtained in good to excellent yields and enantioselectivities.

Supporting Information

 
  • References and Notes

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  • 11 A septum-capped vial with a stirring bar was charged with the corresponding N-Boc imine 2 (0.1 mmol), catalyst 1 (2.8 mg, 2 mol%), and dry toluene (1 mL). The resulting mixture was cooled to –30 °C, before the Chan diene 3 (0.15 mmol) was added via syringe. The resulting reaction mixture was stirred for 3 d. The reaction mixture was quenched by addition of 10% TFA in CH2Cl2 (0.3 mL) at the reaction temperature and diluted with CH2Cl2 (20 mL). The organic phase was washed with sat. NaHCO3 (20 mL) and brine (20 mL). After removing the solvent, the residue was adsorbed onto silica gel and purified by column chromatography (isohexanes–EtOAc, 3:1 to 0:1).

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