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ChemInform Abstract: Enzymes in Organic Chemistry. Part 5. First and Chemo-Enzymatic Synthesis of α-Aminooxyphosphonic Acids of High Enantiomeric Excess.

✍ Scribed by M. DRESCHER; F. HAMMERSCHMIDT


Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Enzymes in Organic Chemistry. Part 5. First and Chemo-Enzymatic Synthesis of α-Aminooxyphosphonic Acids of High Enantiomeric Excess.

-Acyloxyphosphonates (I) are resolved by lipase-catalyzed enantioselective hydrolysis with good to excellent enantiomeric excesses, if hydrolysis is stopped at 30-45% conversion, and the resulting ester is subjected a second time to lipase hydrolysis. The ( R)-enantiomers (II) are obtained by chemical hydrolization of enriched (R)-esters (I). The title acids (IV) are obtained by treatment of resolved enantiomers (II) under modified Mitsunobu conditions and deprotection of the phthalimido derivatives in two steps follows.


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