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Volumn 353, Issue 11-12, 2011, Pages 1923-1926

Rhodium-catalyzed double 1,4-addition of arylboronic acids to β-aryloxyacrylates involving β-oxygen elimination

Author keywords

oxygen elimination; 1,4 addition; boron; esters; rhodium

Indexed keywords


EID: 80052019378     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100253     Document Type: Article
Times cited : (18)

References (37)
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    • 2O (6:1); 69% in EtOH.
    • 2O (6:1); 69% in EtOH.
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    • 3: no reaction; DPPB: 6% 3a and 8% 4a).
    • 3: no reaction; DPPB: 6% 3a and 8% 4a).
  • 16
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    • Asymmetric synthesis of 3,3-diarylpropanoates by rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to cinnamates has been reported. See
    • Asymmetric synthesis of 3,3-diarylpropanoates by rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to cinnamates has been reported. See
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    • For rhodium-catalyzed arylation reactions involving β-oxygen elimination, see
    • For rhodium-catalyzed arylation reactions involving β-oxygen elimination, see
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    • references cited therein.
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    • For rhodium-catalyzed arylation reactions involving β-nitrogen elimination, see
    • For rhodium-catalyzed arylation reactions involving β-nitrogen elimination, see
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    • The stereochemistry of the β-oxygen elimination seems to depend strongly on the solvents used. When the reaction of 1a with one equivalent of 2a was performed in 1,4-dioxane, 3a, (Z)-3-(4-methylphenyl)acrylate (4′a), and 1a were obtained in 26%, 14%, and 55% yields, respectively (cf. Table 1, entry 2).
    • The stereochemistry of the β-oxygen elimination seems to depend strongly on the solvents used. When the reaction of 1a with one equivalent of 2a was performed in 1,4-dioxane, 3a, (Z)-3-(4-methylphenyl)acrylate (4′a), and 1a were obtained in 26%, 14%, and 55% yields, respectively (cf. Table 1, entry 2).
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    • Angew. Chem. Int. Ed. 2009, 48, 7217-7220.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7217-7220
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    • A similar result was also observed at room temperature (96% yield).
    • A similar result was also observed at room temperature (96% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.