Highly diastereoselective hydrophosphonylation of cyclic imines using BINOL as source of chirality

The first highly diastereoselective ( dr up to >95:5) hydrophosphonylation of heterocyclic imines by a chiral phosphorus nucleophile is introduced. Addition of binaphthol ester of phosphorus acid towards BF 3-activated 3-thiazolines gives the corresponding ( aR*,4 R*)-4-thiazolidinylphosphonates...

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Bibliographic Details
Published in:Tetrahedron letters 2000-09, Vol.41 (38), p.7285-7288
Main Authors: Schlemminger, Imre, Lützen, Arne, Willecke, Andreas, Maison, Wolfgang, Koch, Rainer, Saak, Wolfgang, Martens, Jürgen
Format: Article
Language:English
Subjects:
diastereoselection
phosphorus acids and derivatives
thiazolines
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Summary:The first highly diastereoselective ( dr up to >95:5) hydrophosphonylation of heterocyclic imines by a chiral phosphorus nucleophile is introduced. Addition of binaphthol ester of phosphorus acid towards BF 3-activated 3-thiazolines gives the corresponding ( aR*,4 R*)-4-thiazolidinylphosphonates almost exclusively as elucidated by X-ray analysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01265-X