Decarboxylative Radical Addition to Methylideneoxazolidinones for Stereocontrolled Synthesis of Selectively Protected Diamino Diacids
Open Access
- 7 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7270-7273
- https://doi.org/10.1021/acs.orglett.1c02684
Abstract
Syntheses of stereochemically pure and selectively protected diamino diacids can be achieved by redox decarboxylation of distal N-hydroxyphthalimide esters of protected aspartic, glutamic or α-aminoadipic acids via radical addition to methylideneoxazolidinones. The products are useful for solid-supported syntheses of robust bioactive carbocyclic peptide analogs. Yields of reactive primary radical addition are superior to those of more stabilized radicals, and the reaction fails if the alkylideneoxazolidinone has a methyl substituent on its terminus (i.e., 13a/13b).Keywords
Funding Information
- Natural Sciences and Engineering Research Council of Canada (RGPIN-2020-03894)
This publication has 34 references indexed in Scilit:
- Rhodium-catalysed conjugate addition of arylboronic acids to enantiopure dehydroamino acid derivativesOrganic & Biomolecular Chemistry, 2010
- Antimicrobial Leucocin Analogues with a Disulfide Bridge Replaced by a Carbocycle or by Noncovalent Interactions of Allyl Glycine ResiduesJournal of the American Chemical Society, 2006
- Structural insights into stereochemical inversion by diaminopimelate epimerase: An antibacterial drug targetProceedings of the National Academy of Sciences of the United States of America, 2006
- The stereoselective synthesis of aziridine analogues of diaminopimelic acid (DAP) and their interaction with dap epimeraseOrganic & Biomolecular Chemistry, 2005
- Marfey?s reagent for chiral amino acid analysis: A reviewAmino Acids, 2004
- Enantiospecific alkylations of alanineJournal of the Chemical Society, Perkin Transactions 1, 1998
- Free-Radical Reactions in the Synthesis of α-Amino Acids and DerivativesChemical Reviews, 1997
- Diastereoselective radical addition to methyleneoxazolidinones: an enantioselective route to α-amino acidsJournal of the Chemical Society, Chemical Communications, 1995
- A stereoselective synthesis of MeBmt employing a new chiral glycine enolate derivativeThe Journal of Organic Chemistry, 1991
- Diastereoselective radical addition to derivatives of dehydroalanine and of dehydrolactic acidJournal of the Chemical Society, Chemical Communications, 1990