Highly stereoselective aziridine ring-opening with phenylselenide anion and selective intramolecular aldol closure for the enantiopure synthesis of γ-aminocyclopentene derivatives
✍ Scribed by José Alvano Pérez-Bautista; Martha Sosa-Rivadeneyra; Leticia Quintero; Herbert Höpfl; Farid Andrés Tejeda-Dominguez; Fernando Sartillo-Piscil
- Book ID
- 104096805
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 484 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A practical and enantiopure synthesis for the preparation of key intermediates of conformationally locked c-amino acid and nucleoside analogues is described. First, a highly stereoselective aziridine ring-opening reaction with phenylselenide anion was employed for the stereoselective synthesis of the chiral aminoselenide (1S,2S,1 0 S)-8, which after N-benzylation was transformed into the corresponding allyl amine (1S,1 0 S)-7 by oxidation with H 2 O 2 . Then, dihydroxylation-dehomologation of (1S,1 0 S)-7 with (OsO 4 / NMO, NaIO 4 ) selectively afforded the desired c-aminocyclopentene aldehyde (S)-1 and its corresponding c-amino acid (S)-2 via an intramolecular selective aldol-condensation catalyzed by an internal base.