First and Highly Stereoselective Synthesis of Both Enantiomers of Octahydroindole‐2‐phosphonic Acid (OicP)

Abstract

We report the first stereoselective synthesis of (2R,3aR,7aR)‐ and (2S,3aS,7aS)‐octahydroindole‐2‐phosphonic acid 2 (OicP derivatives). The key points are the highly diastereoselective synthesis of cis‐fused bicyclic (3aR,7aR)‐ and (3aS,7aS)‐pyrrolidin‐2‐ones 4 through a dynamic kinetic resolution of racemic γ‐keto acid (±)‐5 with (R)‐ and (S)‐phenylglycinol via Meyers' bicyclic lactams, and the highly diastereoselective addition of trimethyl phosphite to the N‐acyliminium ions 3 obtained from 4.