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Volumn , Issue 15, 2011, Pages 2203-2205

Direct experimental evidence for the epimerization of diastereoisomers in the enantioselective organocatalyzed michael addition of acetoacetates to nitroolefins

Author keywords

asymmetric synthesis; epimerization; Michael addition; organocatalysis; thioureas

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; NITROOLEFIN DERIVATIVE; NITROSTYRENE; STYRENE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

EID: 80052667043     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261139     Document Type: Article
Times cited : (10)

References (39)
  • 32
    • 80052673655 scopus 로고    scopus 로고
    • (3 S)-Ethyl 2-Acetyl-4-nitro-3-phenylbutanoate (4): To a stirred solution of - nitrostyrene (2; 0.30 mmol, 45.6 mg) and catalyst 1 (0.03 mmol, 12.0 mg) in toluene (0.6 mL) was added ethyl acetoacetate (3; 0.60 mmol, 0.08 mL) at [nl]-18C. The reaction mixture was stirred until disappearance of the nitroolefin (observed by TLC). The solvent was removed in vacuo and the residue was purified by flash chromatog-raphy (hexane-EtOAc, 20:1 to 15:1 as eluent) to afford the desired product 4 (0.30 mmol, 83 mg, 99% yield, 54:46 dr, 96:4 er).
    • (3 S)-Ethyl 2-Acetyl-4-nitro-3-phenylbutanoate (4): To a stirred solution of trans - nitrostyrene (2; 0.30 mmol, 45.6 mg) and catalyst 1 (0.03 mmol, 12.0 mg) in toluene (0.6 mL) was added ethyl acetoacetate (3; 0.60 mmol, 0.08 mL) at [nl]-18C. The reaction mixture was stirred until disappearance of the nitroolefin (observed by TLC). The solvent was removed in vacuo and the residue was purified by flash chromatog-raphy (hexane-EtOAc, 20:1 to 15:1 as eluent) to afford the desired product 4 (0.30 mmol, 83 mg, 99% yield, 54:46 dr, 96:4 er).
    • Trans
  • 33
    • 80052671040 scopus 로고    scopus 로고
    • See Supporting Information.
    • See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.