Stereoselective synthesis of δ-amino-β′-hydroxy-β, γ-unsaturated esters by the samarium(II) iodide-mediated aldol reaction of aldehydes with γ,δ-aziridiny-α,β-unsaturated esters

Chemistry Letters

Volumn 34, Issue 3, 2005, Pages 372-373

  Ogawa, Yasuyuki ^a,b   Kuroda, Kiichi ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AZIRIDINE; ESTER DERIVATIVE; SAMARIUM; SAMARIUM IODIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 19444384328     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.372     Document Type: Article

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15. The stereochemistries of the diastereomers were determined by measuring the coupling constants of their derivatives, which were formed by DIBAL reduction and acetonide formation.
16. 2 in THF (0.1 M, 2.40 mL, 0.240 mmol). After the reaction mixture was stirred for 30 min at -78°C, the reaction mixture was quenched with saturated aqueous ammonium chloride and was diluted with ethyl acetate. It was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product was obtained after evaporation of the solvent under reduced pressure and purification by thin-layer chromatography afforded syn-adduct (51.3 mg, 93%).
17. The absolute configuration of 5a was determined by the modified Mosher method.