All Publications


  • Catalytic Chemo-, Regio-, and Enantioselective Bromochlorination of Allylic Alcohols JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Hu, D. X., Seidl, F. J., Bucher, C., Burns, N. Z. 2015; 137 (11): 3795-3798

    Abstract

    Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.

    View details for DOI 10.1021/jacs.5b01384

    View details for Web of Science ID 000351972000018

  • Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY Seidl, F. J., Burns, N. Z. 2016; 12: 1361-1365

    Abstract

    The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene.

    View details for DOI 10.3762/bjoc.12.129

    View details for Web of Science ID 000379393800001

    View details for PubMedID 27559385