Enantioselective synthesis of ( R)- and ( S)- N-Boc-morpholine-2-carboxylic acids by enzyme-catalyzed kinetic resolution: application to the synthesis of reboxetine analogs

The ( R)- and ( S)- N-Boc-morpholine-2-carboxylic acids 9 and 10 were prepared using an enantioselective synthesis employing a highly selective enzyme-catalyzed kinetic resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate ( 11) as the key step. The ( R)- and ( S)- N-Boc-morpholine-2-carbox...

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Bibliographic Details
Published in:Tetrahedron letters 2009-01, Vol.50 (4), p.389-391
Main Authors: Fish, Paul V., Mackenny, Malcolm, Bish, Gerwyn, Buxton, Timothy, Cave, Russell, Drouard, David, Hoople, David, Jessiman, Alan, Miller, Duncan, Pasquinet, Christelle, Patel, Bhairavi, Reeves, Keith, Ryckmans, Thomas, Skerten, Melanie, Wakenhut, Florian
Format: Article
Language:English
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Summary:The ( R)- and ( S)- N-Boc-morpholine-2-carboxylic acids 9 and 10 were prepared using an enantioselective synthesis employing a highly selective enzyme-catalyzed kinetic resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate ( 11) as the key step. The ( R)- and ( S)- N-Boc-morpholine-2-carboxylic acids 9 and 10 were prepared using an enantioselective synthesis employing a highly selective enzyme-catalyzed kinetic resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate ( 11) as the key step. Acids 9 and 10 were then converted efficiently and stereoselectively to reboxetine analogs 3 and 4.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.11.025