1. First and Highly Stereoselective Synthesis of Both Enantiomers of Octahydroindole-2-phosphonic Acid (OicP)
- Author
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Mario Ordóñez, Erick Iván Martínez-Toto, César Eustaquio-Armenta, José Luis Viveros-Ceballos, and Carlos Cativiela
- Subjects
chemistry.chemical_classification ,Bicyclic molecule ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Enantioselective synthesis ,Trimethyl phosphite ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Amino acid ,Kinetic resolution ,chemistry.chemical_compound ,chemistry ,Stereoselectivity ,Physical and Theoretical Chemistry ,Enantiomer - 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.
- Published
- 2017
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