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- Title
Asymmetric Access to α-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile.
- Authors
Ben Ayed, Kawther; Beauchard, Anne; Poisson, Jean‐François; Py, Sandrine; Laurent, Mathieu Y.; Martel, Arnaud; Ammar, Houcine; Abid, Souhir; Dujardin, Gilles
- Abstract
Enantiopure vinyl ethers of Stericol® underwent diastereoselective thermal 1,3 dipolar cycloadditions with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomerically and enantiomerically pure crystalline NH-isoxazolidine, the absolute configuration of which was established by X-ray crystallography. N-Protection and N-O cleavage of this isoxazolidine gave enantioenriched quaternary aspartate derivatives bearing functionalized side chains.
- Subjects
VINYL ethers; CHEMICAL synthesis; RING formation (Chemistry); AMINO acids; HETEROCYCLIC compounds; ASPARTATES
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 14, p2924
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301739