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An efficient and simple new stereocontrolled access route to novel disubstituted cispentacin derivatives with multiple stereogenic centers from norbornene β‐lactam has been developed. The synthesis involves olefinic bond functionalization by dihydroxylation followed by oxidative ring cleavage and transformation of the dialdehyde intermediate through a Wittig reaction.

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The stereocontrolled syntheses of functionalized acyclic β2,3‐amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis‐ and trans‐2‐aminocyclopent‐3‐enecarboxylates, which were derived from a racemic bicyclic β‐lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C–C double bond of the cyclopentene β‐amino esters. The subsequent NaIO4‐mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction.