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Friday, August 05, 2005

Asymmetric synthesis of monohydroxy tetradecanoic acids

Methyl 3-, 6- and 13-oxo tetradecanoates went through reduction with NaBH4 in the presence of 1,2:5,6-di-O-isopropylidene-Dglucofuranose (DIPGH) and menthol together with isovaleric and pivalic acids in THF solution. This work signifies the importance of positional
effect. The position of lower steric hinderance and higher enantiomeric excess and asymmetric reduction yield were noted down, namely the prochiral 13-keto isomer structures.
With this asymmetric reduction at normal atmospheric pressure together with inexpensive auxiliaries make it competitive with other reduction methods and is needed to assess the need in the market. Here's a link for this article


  • 3/10 marks.
    1) your molecules are unreadable in the blog and barely readable when expanded
    2) one of your redundant schemes is too wide
    3) Your assignment consists of picking a SINGLE specific reaction showing starting material, reagents over the arrow and the products. What you did is just copy one of the schemes in the paper and the molecules you drew make no chemical sense (e.g. parentheses without number of repeating units)
    4) no page number in CiteULike
    5) your description has nothing to do with the scheme - e.g. where is the borohydride in the scheme that you mention?

    By Blogger Jean-Claude Bradley, at 7:16 AM  

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