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Volumn , Issue 10, 2008, Pages 1565-1570

The effectiveness of proteinogenic amino acids in the asymmetric aldol reaction in DMSO and aqueous DMSO

Author keywords

asymmetric synthesis, aldol reactions, organocatalyst, amino acids, water

Indexed keywords

AMINO ACID; DIMETHYL SULFOXIDE; HISTIDINE; KETONE DERIVATIVE; PROLINE; SERINE;

EID: 46649117893     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077789     Document Type: Article
Times cited : (31)

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    • Typical Experimental Procedure (Table 1, To a DMSO solution (0.40 mL) or aq DMSO solution (DMSO: 0.40 mL; H2O: 22 μL) of amino acid (0.12 mmol) were added p- nitrobenzaldehyde (60.5 mg, 0.4 mmol) and cyclohexanone (207 μL, 2.0 mmol) under an argon atmosphere at r.t. When the reaction was complete, it was quenched with pH 7.0 phosphate buffer solution. The organic materials were extracted with EtOAc (3 x) and the combined organic extracts were dried over anhyd Na2SO4, and concentrated in vacuo after filtration. The residue was purified by flash chromatography to give an aldol product. Diastereoselectivity was determined by 1H NMR (400 MHz, Enantiomeric excess was determined by HPLC analysis with a Chiralpak AS-H column hexane-2-pro-panol, 10:1, λ, 231 nm, 1.0 mL/min; major enantiomer tR= 11.5 min, minor enantiomer tR, 18.7 min
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.