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Chiral nitrogen-metal complexes for the asymmetric reduction of ketones

✍ Scribed by Rob ter Halle; Alexandra Bréhéret; Emmanuelle Schulz; Catherine Pinel; Marc Lemaire

Book ID
104361243
Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
509 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

Chiral cobalt--diamine complexes have been prepared and tested in catalytic reduction of 13-ketoesters and ketones with molecular hydrogen or hydride transfer reduction (HTR). Modest to high conversions, but low e.e.s were obtained in the first case, whereas encouraging e.e.s (up to 58%) but low conversions were observed in the reduction of acetophenone by HTR. Synthesis of chiral nitrogen tetradentate ligands for Co, lr and Rh are described. Furthermore, (IR,2R)-(-)-N-tosyl-l,2-ethanediamine proved to be a particularly efficient ligand for iridium in the hydride transfer reduction of acetophenone (87% conversion, 92% e.e.).

📜 SIMILAR VOLUMES

Chiral thiourea as ligand for the asymme
Chiral thiourea as ligand for the asymmetric reduction of prochiral ketones
✍ François Touchard; Patrick Gamez; Fabienne Fache; Marc Lemaire 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 265 KB

The catalytic enantioselective reduction of prochiral ketones using a chiral thiourea as ligand is reported. Several metallic precursors were tested. e.e.'s up to 94% are obtained with a ruthenium complex.