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.hodgson
chem.ox.ac.uk
D. M. Hodgson, T. Arif, J. Am. Chem. Soc., 2008, 130, 16500-16501.
DOI: 10.1021/ja8076999
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].
see article for more examples
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
