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

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, Org. Lett., 2010, 12, 4204-4207.

DOI: 10.1021/ol101843q (free Supporting Information)


Abstract

β-Lithiooxyphosphonium ylides, generated in situ from aldehydes and Wittig reagents, react readily with halomethyl esters to form trisubstituted Z-allylic esters. The methodology was applied to a total synthesis of a geranylgeraniol-derived diterpene.

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

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


Key Words

Schlosser Reaction, Allylic Alcohols


ID: J54-Y2010-2660