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SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS
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UNSPECIFIED (1993) SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS. TETRAHEDRON-ASYMMETRY, 4 (4). pp. 743-756. ISSN 0957-4166
Full text not available from this repository.Abstract
A multistep synthesis resulting in a good yield of the title compound has been developed based on the Pd-catalysed coupling of 1-chloroisoquinoline and 2-methoxy-1-naphthylboronic acid (5). The product is converted into the corresponding tfifluoromethanesulphonate (10) by successive demethylation and treatment with (CF3CO)2O, followed by a further Pd-catalysed coupling with Ph2P(O)H. The resulting phosphine oxide (11) was cleanly reduced with HSiCl3. Resolution of the phosphinamine (4) was carried out with the Pd complex derived from (R)-(+)-dimethyl(1-(1-naphthyl)ethyl)amine and PdCl2; the diastereomers were of different stabilities and solubilities and were therefore readily separated. The resolved phosphinamine, [alpha]D22 +/- 153 (c = 1, CHCl3), was enantiomerically stable on heating to 65-degrees-C for 24h. X-ray crystal structures of the adduct (16) and the Pd dimer (7) isolated during the initial coupling reaction are presented.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | TETRAHEDRON-ASYMMETRY |
| Publisher: | PERGAMON-ELSEVIER SCIENCE LTD |
| ISSN: | 0957-4166 |
| Date: | April 1993 |
| Volume: | 4 |
| Number: | 4 |
| Number of Pages: | 14 |
| Page Range: | pp. 743-756 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/21426 |
Data sourced from Thomson Reuters' Web of Knowledge
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