Abstract

AbstractA 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

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