Highly stereoselective aziridine ring-opening with phenylselenide anion and selective intramolecular aldol closure for the enantiopure synthesis of γ-aminocyclopentene derivatives |
| |
Authors: | Jos Alvano Prez-Bautista Martha Sosa-Rivadeneyra Leticia Quintero Herbert Hpfl Farid Andrs Tejeda-Dominguez Fernando Sartillo-Piscil |
| |
Institution: | aCentro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq, San Claudio, San Manuel, 72570 Puebla, Mexico;bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Mexico |
| |
Abstract: | A practical and enantiopure synthesis for the preparation of key intermediates of conformationally locked γ-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′S)-8, which after N-benzylation was transformed into the corresponding allyl amine (1S,1′S)-7 by oxidation with H2O2. Then, dihydroxylation–dehomologation of (1S,1′S)-7 with (OsO4/NMO, NaIO4) selectively afforded the desired γ-aminocyclopentene aldehyde (S)-1 and its corresponding γ-amino acid (S)-2 via an intramolecular selective aldol-condensation catalyzed by an internal base. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|