Display Settings:

Format

Send to:

Choose Destination
    J Org Chem. 2006 Feb 17;71(4):1537-44.

    Boron trifluoride-induced, new stereospecific rearrangements of chiral epoxy ethers. Ready access to enantiopure 4-(diarylmethyl)-1,3-dioxolanes and 4,5-disubstituted tetrahydrobenzo[c]oxepin-4-ols.

    Source

    Departament de Química Orgànica and Parc Científic de Barcelona, Universitat de Barcelona, 08028 Barcelona, Spain.

    Abstract

    Upon treatment with BF3.Et2O at low temperature, enantiopure benzyl-type ethers of arylglycidols with electron withdrawing substituents at the skeletal aryl group and electron donating substituents at the benzyl group undergo stereospecific rearrangements of Friedel-Crafts type, leading to enantiopure 4-diarylmethyl-1,3-dioxolanes (2) or to enantiopure trans-4,5 disubstituted tetrahydrobenzo[c]oxepin-4-ols (5). The course of the reactions is controlled by the substitution pattern at the benzyl ether: While benzylic systems activated toward ipso substitution afford diarylmethanes 2 through a Friedel-Crafts reaction followed by fragmentation, benzylic systems activated toward ortho attack lead to enantiopure oxepinols 5 through a 7-endo-tet ring closure of Friedel-Crafts type.

    PMID:
    16468802
    [PubMed - indexed for MEDLINE]

      Supplemental Content

      Icon for American Chemical Society

      Save items

      loading

      Recent activity

      Your browsing activity is empty.

      Activity recording is turned off.

      Turn recording back on

      See more...
      Write to the Help Desk