| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348137 | Tetrahedron: Asymmetry | 2007 | 6 Pages |
The synthesis of novel P-stereogenic phenylphosphonamides 3 and 11 via an intramolecular nucleophilic substitution of P-stereogenic phosphoramide 8 is described. These compounds were used as chiral Lewis basic catalysts for the asymmetric allylation of benzaldehyde, providing the corresponding homoallylic alcohol derivatives in up to 54% ee.
Graphical abstractWe succeeded in the synthesis of novel P-stereogenic phenylphosphonamides, which could be utilized as chiral Lewis basic catalysts for asymmetric allylation of benzaldehyde using allyltrichlorosilane.Figure optionsDownload full-size imageDownload as PowerPoint slide
(1S,4aR)-(4a-Oxo-4-phenyl-1,2,3,4,4a,9-hexahydro-4,9a-diaza-4aλ5-phospha-fluoren-1-ylmethyl)-phenyl-amineC23H24N3OPEe = 100%[α]D23=+335.3 (c 0.25, CHCl3)Source of chirality: (S)-aspartic acidAbsolute configuration: (S,RP)
(1S,4aR)-N-(4a-Oxo-4-phenyl-1,2,3,4,4a,9-hexahydro-4,9a-diaza-4aλ5-phospha-fluoren-1-ylmethyl)-N-phenyl-benzamideC30H28N3O2PEe = 100%[α]D23=+68.8 (c 0.83, CHCl3)Source of chirality: (S)-aspartic acidAbsolute configuration: (S,RP)
