Diastereoselective synthesis of chiral non-racemic 2-substituted 2-boranatophosphino ethanoic acid: a potential intermediate to chiral ligands for asymmetric catalysis

Chiral α-amidophosphine boranes 7a– b can be diastereoselectively alkylated, using a phenylglycinol derivative as a chiral inducer, to furnish α-substituted α-amidophosphine boranes 8– 12 with up to 99% diastereoisomeric excess. Selective reduction of the amidophosphine boranes afforded optically pu...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2003-06, Vol.14 (12), p.1637-1644
Main Authors: Ebran, Jean-Philippe, Jubault, Philippe, Pannecoucke, Xavier, Quirion, Jean-Charles
Format: Article
Language:English
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Summary:Chiral α-amidophosphine boranes 7a– b can be diastereoselectively alkylated, using a phenylglycinol derivative as a chiral inducer, to furnish α-substituted α-amidophosphine boranes 8– 12 with up to 99% diastereoisomeric excess. Selective reduction of the amidophosphine boranes afforded optically pure β-boranatophosphine-alcohol 13. The latter one can then be oxidized in boronatophosphine acid 14. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00287-8