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Volumn 5, Issue 5, 2014, Pages 1799-1803

Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: Highly enantioselective Friedel-Crafts reaction of indoles with β,β-disubstituted nitroalkenes

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; NITROALKENES; QUATERNARY CENTERS; STEREOSELECTIVE CONSTRUCTION;

EID: 84898071338     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc53542h     Document Type: Article
Times cited : (77)

References (95)
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    • For selected examples of Michael-type Friedel-Crafts reaction of indoles with α,β-unsaturated carbonyl compounds, see
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    • Wu, J.1    Li, X.2    Wu, F.3    Wan, B.4
  • 54
    • 84871025337 scopus 로고    scopus 로고
    • For the asymmetric cyanation of β,β-disubstituted α,β-unsaturated carbonyl compounds or nitroalkenes, see
    • K. Akagawa K. Kudo Angew. Chem., Int. Ed. 2012 51 12786
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 12786
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  • 63
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    • For the asymmetric Michael reaction of β-alkoxycarbonyl nitrostyrene with aldehyde, see
    • R. Liu J. Zhang Chem.-Eur. J. 2013 19 7319
    • (2013) Chem.-Eur. J. , vol.19 , pp. 7319
    • Liu, R.1    Zhang, J.2
  • 64
    • 84880139921 scopus 로고    scopus 로고
    • During preparation of the manuscript, Gong and Meggers reported the same kind of Michael-type asymmetric Friedel-Crafts reaction of indole with β,β-disubstituted nitroalkenes catalyzed by Ni-BOX complex
    • R. Kastl H. Wennemers Angew. Chem., Int. Ed. 2013 52 7228
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 7228
    • Kastl, R.1    Wennemers, H.2
  • 75
    • 80053992962 scopus 로고    scopus 로고
    • See also references cited therein The configuration of α-methoxycarbonyl-β-nitrostyrene 5h was determined to be Z by X-ray analysis, and those of the other substrates were determined by analogy The relative stereochemistry of 8 was determined by X-ray analysis of the N-free tetrahydro-β-carboline (see ESI) See ESI For theoretical studies on chiral phosphoric acid catalysis, see
    • M. Rueping A. Kuenkel I. Atodiresei Chem. Soc. Rev. 2011 40 4539
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 4539
    • Rueping, M.1    Kuenkel, A.2    Atodiresei, I.3
  • 93
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    • For a theoretical study on chiral phosphoric acid catalyzed Friedel-Crafts reaction of indole with nitrostyrene, see
    • Y. Shibata M. Yamanaka J. Org. Chem. 2013 78 3731
    • (2013) J. Org. Chem. , vol.78 , pp. 3731
    • Shibata, Y.1    Yamanaka, M.2
  • 94
    • 79251482773 scopus 로고    scopus 로고
    • For DFT calculation of Friedel-Crafts reaction of 4,7-dihydroindole with nitrostyrene, see
    • T. Hirata M. Yamanaka Chem.-Asian J. 2011 6 510
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    • Hirata, T.1    Yamanaka, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.