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Convergent and Stereoselective Synthesis of Trisubstituted E-Alkenyl Bromides and Iodides via β-Oxido Phosphonium Ylides

David M. Hodgson* and Tanzeel Arif

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom, Email: david.hodgsonchem.ox.ac.uk

D. M. Hodgson, T. Arif, J. Am. Chem. Soc., 2008, 130, 16500-16501.

DOI: 10.1021/ja8076999 (free Supporting Information)


Abstract

β-Oxido phosphonium ylides, generated in situ from aldehydes and Wittig reagents react readily with electrophilic halogen sources to form predominantly or exclusively E-bromo- or iodosubstituted alkenes. The stereochemical outcome on halogenation is remarkably sensitive to alkylidene size [ethylidene(triphenyl)phosphorane is highly Z-selective].

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Convergent Synthesis of Trisubstituted Z-Allylic Esters by Wittig-Schlosser Reaction

D. M. Hodgson, T. Arif, Org. Lett., 2010, 12, 4204-4207.


Key Words

Schlosser Modification, Alkenyl Bromides, Alkenyl Iodides, Olefination


ID: J48-Y2008-3750