A general approach to enantiomeric γ-aminophosphonic acids using chiral sulfinimine methodology

✍ Scribed by Piotr Łyżwa; Marian Mikołajczyk

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 308 KB
• Volume: 22
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20710

✦ Synopsis

Abstract

A new approach to asymmetric synthesis of γ‐aminophosphonic acids is described. It involves the diastereoselective addition of various carbon and phosphorus nucleophiles to enantiopure (+)‐(S)‐N‐[(3‐diethoxyphosphoryl)propylidene]‐p‐toluenesulfinamide and subsequent acid hydrolysis of the adducts formed. The utility of the method is illustrated by the synthesis of (+)‐(S)‐2‐ amino‐4‐phosphonobutanoic acid (AP4), and both enantiomerically enriched (–)‐(R)‐ and (+)‐(S)‐1‐amino‐propane‐1,3‐diphosphonic acid. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:594–598, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20710