Scandium at Work

Errr:

Junji Inanaga
at Kyushu University, in Japan, and colleagues recently explored chiral
rare earth metal complexes with fluorinated organophosphate ligands in
the enantioselective fluorination of β-ketoesters (Tet. Asym. 2006, 17,
504). "Previously published methods have been applied to bulky esters,"
Inanaga says, "while ours can be applied to popularly used small
esters, such as methyl ester." Using a scandium catalyst in combination
with a 1-fluoropyridinium triflate fluorinating reagent, the
researchers achieved yields as high as 94% with 84% enantiomeric excess
(ee).

Nope, I don’t know what it means either but sounds terribly sexy don’t it?

4 responses

  1. It’s all about selectively making the left (or right-handed) version of a chemical rather than, as normally happens, a mixture of the two.
    The two versions (or enantiomers) can have radically different properties – the most famous example of this is thalidomide where the anti-morning sickness property was due to one enantiomer, while the disastrous side-effects where due to the other.
    If you can make them selectively then you might be able to separate the two properties.
    See, simple really. 🙂

  2. Not sure why you want to flourinate a small molecule like methyl ester but I suspect it would be an intermediate to some chiral drug such as (IIRC) a number of statins

  3. BTW the abstract was readily located at Scirus / science driect – http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THT-4J9N0PJ-1&_coverDate=02%2F20%2F2006&_alid=410608057&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5291&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=688ba29427232ed651ac4f4fd32783ca
    if you know the author anf the year published then scirus (http://www.scirus.com/search_simple/ ) is very vrey good at getting you the abstracts and sometimes the full text

  4. The Remittance Man Avatar
    The Remittance Man

    But, Wilbur. Will it fly?
    RM

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