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Synthesis of Enantiomerically Pure Isoxazolidine Monomers for the Preparation of β 3 ‐Oligopeptides by Iterative α ‐Keto AcidHydroxylamine (KAHA) Ligations
Author(s) -
Chiang YingLing,
Russak Justin A.,
Carrillo Nancy,
Bode Jeffrey W.
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200484
Subject(s) - hydroxylamine , chemistry , monomer , oligopeptide , combinatorial chemistry , enantioselective synthesis , cycloaddition , stereochemistry , organic chemistry , polymer chemistry , polymer , peptide , biochemistry , catalysis
A versatile method for the synthesis of enantiomerically pure isoxazolidine monomers for the synthesis of β 3 ‐oligopeptides via α ‐keto acidhydroxylamine (KAHA) ligation is presented. This one‐pot synthetic method utilizes in situ generated nitrones bearing gulose‐derived chiral auxiliaries for the asymmetric 1,3‐dipolar cycloaddition with methyl 2‐methoxyacrylate. The resulting enantiomerically pure isoxazolidine monomers bearing diverse side chains (proteinogenic and non‐proteinogenic) can be synthesized in either configuration ( like ‐ and unlike ‐configured). The scalable and enantioselective synthesis of the isoxazolidine monomers enables the use of the synthesis of β 3 ‐oligopeptides via iterative α ‐keto acidhydroxylamine (KAHA) ligation.