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EPSRC Reference: GR/N00647/01
Title: MULTI-COMPONENT COUPLINGS ON A ZIRCONOCENE TEMPLATE
Principal Investigator: Whitby, Professor RJ
Other Investigators:
Researcher Co-Investigators:
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Department: Sch of Chemistry
Organisation: University of Southampton
Scheme: Standard Research (Pre-FEC)
Starts: 13 December 1999 Ends: 12 June 2001 Value (£): 59,659
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors
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Summary on Grant Application Form
In organic synthesis there is a great need for new synthetic methods which combine several components efficiently, both for the synthesis of complex targets, and to provide access to large numbers of compounds for biological testing. The little investigated insertion of metal carbenoids into metal-carbon bonds holds particular promise since the product retains the organometallic functionality of the starting material.We propose to develop some generally useful synthetic transformations using this idea including:The insertion of alkyl carbenoid into a vinyl-zirconium species (from hydrozirconation of an alkyne) provides a novel convergent route to allylmetallic reagents which may be further elaborated with a wide range of electrophiles. Variation of the carbenoid fragment should provide access to a variety of functionalised systems.Insertion of vinyl-carbenoid into an organozirconium provides a vinylzirconium species which may be further elaborated provided a versatile stereospecific synthesis of alkenes, dienes, etc. Insertion of metallated epoxides, followed by elimination of zirconium oxide, provide access to a complementary range of alkenes.Insertion of metallated sulphonyl epoxides into organozirconium species forms zirconated epoxides which rearrange to zirconium enolates. This provides a unique, convergent, regiospecific and possibly stereospecific synthesis of enolates - key intermediates in organic synthesis.
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Organisation Website: http://www.soton.ac.uk