June 06, 2006
Scandium at Work
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?
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. :-)
Posted by: Bishop Hill | Jun 6, 2006 8:49:05 AM
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
Posted by: Francis | Jun 6, 2006 12:09:22 PM
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
Posted by: Francis | Jun 6, 2006 12:21:10 PM
But, Wilbur. Will it fly?
Posted by: The Remittance Man | Jun 6, 2006 5:43:38 PM