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Synlett 2015; 26(06): 807-809
DOI: 10.1055/s-0034-1379999
DOI: 10.1055/s-0034-1379999
letter
Disulfonimide-Catalyzed Asymmetric Synthesis of δ-Amino-β-Keto Esters
Weitere Informationen
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.
Key words
chiral disulfonimides - δ-amino-β-keto esters - Chan diene - N-Boc imines - vinylogous Mukaiyama–Mannich reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379999.
- Supporting Information
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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).
For contributions from other groups after our seminal report, see: