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Volumn 66, Issue 34, 2010, Pages 6965-6976

The attempted stereoselective synthesis of chiral 2,2′-biindoline

Author keywords

Biindoline; Chiral biamines; Helical chiral ligands; Metathesis; Sharpless AD

Indexed keywords

2,2' BIINDOLINE; AMINE; PHENOL; UNCLASSIFIED DRUG;

EID: 77955469755     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.035     Document Type: Article
Times cited : (14)

References (32)
  • 4
    • 77955473809 scopus 로고    scopus 로고
    • note
    • There is one reference to 2,2′-biindoline in the literature which accomplishes its synthesis in a non-stereoselective fashion by radical dimerization of indoline - see: Naarmann, H.; Zdenek, J.; Viehe, H.G.; Beaujean, M.; Merenyi, R. German Patent DE 2,934,131, 1981. This report does not provide spectral data.
  • 7
    • 1942500258 scopus 로고    scopus 로고
    • A small quantity (5%) of the symmetrical byproduct N,N-diBoc-1,3-bis(2- allylphenyl)urea was also produced but was easily removed by crystallisation from the reaction mixture. A white byproduct from this reaction has been previously reported, however its structure was not identified - see: P.D. Knight, I. Munslow, P.N. O'Shaughnessy, and P. Scott Chem. Commun. 2004 894 895 Presumably, this is the same urea
    • (2004) Chem. Commun. , pp. 894-895
    • Knight, P.D.1    Munslow, I.2    O'Shaughnessy, P.N.3    Scott, P.4
  • 8
    • 77955467731 scopus 로고    scopus 로고
    • note
    • The ee discrepancy is in agreement with the literature in that trans olefins are dihydroxylated with higher stereochemical purity by ADmix β, see Ref. 7.
  • 12
    • 77955470544 scopus 로고    scopus 로고
    • note
    • This mixture was obtained from the inseparable cis and trans isomers formed from metathesis using Grubbs' I catalyst.
  • 13
    • 77955470621 scopus 로고    scopus 로고
    • note
    • The yields quoted were based on the quantity of each diastereomer present in the starting mixture.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.