메뉴 건너뛰기




Volumn 351, Issue 18, 2009, Pages 3186-3192

Catalytic asymmetric synthesis of branched chiral allylic phenyl ethers from (E)-allylic alcohols

Author keywords

Asymmetric catalysis; Organometallic compounds; Palladium; Synthetic methods

Indexed keywords


EID: 73349129970     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900678     Document Type: Article
Times cited : (34)

References (48)
  • 3
    • 30944458188 scopus 로고    scopus 로고
    • For examples of asymmetric allylation of phenols with allylic alcohol derivatives not included in ref.[1, see: a Y. Uozumi, M. Kimura, Tetrahedron: Asymmetry 2006, 17, 161-166;
    • [1], see: a) Y. Uozumi, M. Kimura, Tetrahedron: Asymmetry 2006, 17, 161-166;
  • 13
    • 39849107380 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 1454-1457;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 1454-1457
  • 21
    • 14844297329 scopus 로고    scopus 로고
    • For the related reaction to form 3-acyloxy-1-alkenes in high enantiomeric purity, see
    • For the related reaction to form 3-acyloxy-1-alkenes in high enantiomeric purity, see: S. F. Kirsch, L. E. Overman, J. Am. Chem. Soc. 2005, 127, 2866-2867.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 2866-2867
    • Kirsch, S.F.1    Overman, L.E.2
  • 26
    • 73349133590 scopus 로고    scopus 로고
    • For selected examples of the catalysis of allylic imidate rearrangements with other chiral palladium (II) complexes, see: a) D. F. Fischer, Z.-Q. Xin, R. Peters, Angew. Chem. 2007, 119, 7848-7851;
    • For selected examples of the catalysis of allylic imidate rearrangements with other chiral palladium (II) complexes, see: a) D. F. Fischer, Z.-Q. Xin, R. Peters, Angew. Chem. 2007, 119, 7848-7851;
  • 27
    • 35048826146 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7704-7707;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 7704-7707
  • 39
    • 73349083265 scopus 로고    scopus 로고
    • CCDC 748079 (a) and CCDC 748078 (b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
    • CCDC 748079 (a) and CCDC 748078 (b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
  • 40
    • 73349112444 scopus 로고    scopus 로고
    • [13b].
    • [13b].
  • 43
    • 73349117700 scopus 로고    scopus 로고
    • 2 in pivalic acid at 85°C; however, removal of excess pivalic acid is cumbersome.
    • 2 in pivalic acid at 85°C; however, removal of excess pivalic acid is cumbersome.
  • 45
    • 73349096192 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 46
    • 73349119568 scopus 로고    scopus 로고
    • In favorable cases where the nucleophile is phenol or an unhindered electron-poor substituted phenol, the transformation can undoubtedly be carried out in satisfactory fashion using lower catalyst loadings
    • In favorable cases where the nucleophile is phenol or an unhindered electron-poor substituted phenol, the transformation can undoubtedly be carried out in satisfactory fashion using lower catalyst loadings.
  • 47
    • 73349133214 scopus 로고    scopus 로고
    • 2 are available from Aldrich Chemical Co.
    • 2 are available from Aldrich Chemical Co.
  • 48
    • 73249153734 scopus 로고    scopus 로고
    • The origin of these differences is not yet fully understood. We note that an external anionic ligand has been shown to be coordinated to palladium during the ratedetermining step of the rearrangement of allylic trichloroacetimidates catalyzed by [COP-Cl2, 8a] whereas both the double bond and the imidate nitrogen have been proposed to be bound to palladium during the reaction of allylic trichloroacetimidates with carboxylate nucleophiles.[7
    • [7]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.