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    Synthesis of (3S)-(+)-diethyl-2-(l-oxoethyl)-5-phenyl-(3 N-p-Toluenesulfinamido) pentylphosphonate

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    2004_BrensdalK_THS_000779.pdf (1.955Mb)
    Author
    Brensdal, Kelli
    Advisor
    Ron Wilde; Barry Ferst; Marilyn Schendel
    Date of Issue
    2004-04-01
    Metadata
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    URI
    https://scholars.carroll.edu/handle/20.500.12647/178
    Title
    Synthesis of (3S)-(+)-diethyl-2-(l-oxoethyl)-5-phenyl-(3 N-p-Toluenesulfinamido) pentylphosphonate
    Type
    thesis
    Abstract
    It has been found that reactions between pentacovalent oxaphospholenes (P(V)) and various electrophiles produced substituted phosphonates under mild conditions. Using an imine as an electophile with the oxaphospholene would produce a y-phosphono amino acid. However, simple imines are not good enough electrophiles to react with a standard P(V) compound. Imines with attached electron withdrawing sulfoxide groups proved to be better electrophiles. The imine was prepared by the reaction of hydrocinnamaldehyde with p-toluenesulfmamide to produce (S)-(+)-N-(3-phenyl)- propyl-p-toluenesulfmamide which was then treated with 2,2,2-triethoxy-2,2-dihydro-5- methyl-l,2X5-oxaphospholene (P(V)) with MgBr2 as a Lewis acid to produce the desired product, (3S)-(+)-diethyl-2-(1-oxoethyl)-5-phenyl-(3-N-p-toluenesulfinamido) pentylphosphonate.
    Degree Awarded
    Bachelor's
    Semester
    Spring
    Department
    Chemistry & Physics
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    • Chemistry and Physics Undergraduate Theses

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