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

✍ Scribed by Jean-Philippe Ebran; Philippe Jubault; Xavier Pannecoucke; Jean-Charles Quirion

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 296 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00287-8

✦ Synopsis

Chiral a-amidophosphine boranes 7a-b can be diastereoselectively alkylated, using a phenylglycinol derivative as a chiral inducer, to furnish a-substituted a-amidophosphine boranes 8-12 with up to 99% diastereoisomeric excess. Selective reduction of the amidophosphine boranes afforded optically pure b-boranatophosphine-alcohol 13. The latter one can then be oxidized in boronatophosphine acid 14.