On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICl-NaOMe or ICl-pyridine |
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| Authors: | Andrew P Lightfoot Andrew Whiting |
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| Institution: | a GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK
b Department of Chemistry, Science Laboratories, University of Durham, South Road, Durham DH1 3LE, UK |
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| Abstract: | Conversion of hindered alkenyl boronate esters into the corresponding iodoalkene, or alkenyl chloride can be carried out stereoselectively using ICl. In the presence of NaOMe, direct reaction of ICl is favoured yielding the E-iodoalkene, however, the reaction with ICl followed by NaOMe can be used to give different major alkenyl iodide and chloride products, depending upon reaction temperature, ICl source and alkenyl boronate stereoelectronics. |
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| Keywords: | Alkenyl boronate Boronate esters Iodo-deboronation Chloro-deboronation Iodine-monochloride |
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