Temporary Protection of H‐Phosphinic Acids as a Synthetic Strategy

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 27; pp. 4646 - 4654
• Main Authors: Coudray, Laëtitia, Montchamp, Jean‐Luc
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 01.09.2009; Wiley; Wiley-VCH
• Subjects: Chemistry; Chemistry, Organic; Cross‐coupling; Exact sciences and technology; Metathesis; Organic chemistry; Organometalloidal and organometallic compounds; P derivatives; Palladium; Phosphorus; Physical Sciences; Preparations and properties; Science & Technology; Synthetic ­methods; HYPOPHOSPHOROUS ACID; ANALOGS; ALKYLATION; Metathesis; Phosphorus; Palladium; CARBON BOND FORMATION; CROSS-COUPLING REACTIONS; Cross-coupling; RING-CLOSING METATHESIS; ASYMMETRIC DIHYDROXYLATION; Synthetic methods; DERIVATIVES; CATALYZED DEHYDRATIVE ALLYLATION; Phosphinic acids; Organic phosphinate; Kynureninase; Phosphorus Organic compounds; Asymmetric synthesis; Aspartate carbamoyltransferase; Cross reaction; Chemical synthesis; Platinoid; Protection; Enzyme; Transferases; Enzyme inhibitor; Transition metal; Olefin; Sharpless dihydroxylation; Hydrolases; Orthoester; Ethylenic compound; Ruthenium complex; Cross-Coupling; Synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200900694

H‐Phosphinates obtained through various methodologies are protected directly by the reaction with triethyl orthoacetate. The resulting products can be manipulated easily, andvarious synthetic reactions are presented. For example, application to the synthesis of aspartate transcarbamoylase (ATCase) or kynureninase inhibitors are illustrated. Other reactions, such as Sharpless' asymmetric dihydroxylation, or Grubbs' olefin cross‐metathesis are also demonstrated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Because numerous organic reactions are not compatible with the presence of a P–H bond, the temporary protection of the P–H bond of H‐phosphinates was investigated.Our methods have expanded the scope of available H‐phosphinate starting materials. Various applications of the protection strategy are presented.