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N-acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents


Reference:

Taylor, J. E., Williams, J. M. J. and Bull, S.D., 2012. N-acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents. Tetrahedron Letters, 53 (32), pp. 4074-4076.

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    Official URL:

    http://dx.doi.org/10.1016/j.tetlet.2012.05.108

    Abstract

    Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN·BPh 4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed by filtration, providing the ester products without the need for further purification.

    Details

    Item Type Articles
    CreatorsTaylor, J. E., Williams, J. M. J. and Bull, S.D.
    DOI10.1016/j.tetlet.2012.05.108
    DepartmentsFaculty of Science > Chemistry
    Publisher StatementTaylor_Tetrahedron_Letters_2012.pdf: NOTICE: this is the author’s version of a work that was accepted for publication inTetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 53, issue 32, 2012, DOI 10.1016/j.tetlet.2012.05.108
    RefereedYes
    StatusPublished
    ID Code31002

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