Hydrolysis stereospecific ester cleavage

Phosphonates and phosphonamidates, which mimic the tetrahedral geometry and anionic character of the transition state for hydrolysis, have proven especially reliable as haptens. Antibodies generated against such compounds readily promote the cleavage of esters and, in a few cases, amides. High levels of stereospecificity are attainable even at chiral centers remote from the reaction site [11]. 

Compound (1) and its enantiomer provide a variation on the same theme of stereospecific reductive amination. In this case, reduction of a chiral cyclic hydrazone (derived from an a-keto acid and (1)) with Aluminum Amalgam in wet DME proceeds with high stereoselectivity. Reductive cleavage of the N-N bond and ester hydrolysis complete the procedure, which produces a-amino acids with high optical purity (eq 4). The source of chirality is recovered by conversion of the resulting indoline-2-methanol back into (1). ... 

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