Literature DB >> 12889919

Photolysis of diacyl peroxides: a radical-based approach for the synthesis of functionalized amino acids.

M Daniel Spantulescu1, Rajendra P Jain, Darren J Derksen, John C Vederas.   

Abstract

[reaction: see text] Photolysis of the amino acid derived symmetrical and unsymmetrical diacyl peroxides at 254 nm at low temperature (-78 to -196 degrees C) generates various bis(amino acids) in a concise manner and with orthogonal protection. The methodology was applied to the synthesis of (4R)-5-propyl-L-leucine (PrLeu), a component of HUN-7293.

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Year:  2003        PMID: 12889919     DOI: 10.1021/ol035125y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Aspartate-catalyzed asymmetric epoxidation reactions.

Authors:  Gorka Peris; Charles E Jakobsche; Scott J Miller
Journal:  J Am Chem Soc       Date:  2007-06-26       Impact factor: 15.419

2.  Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues.

Authors:  Charles E Jakobsche; Gorka Peris; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Directed heterodimerization: stereocontrolled assembly via solvent-caged unsymmetrical diazene fragmentation.

Authors:  Mohammad Movassaghi; Omar K Ahmad; Stephen P Lathrop
Journal:  J Am Chem Soc       Date:  2011-08-01       Impact factor: 15.419

4.  Chemoselective and enantioselective oxidation of indoles employing aspartyl peptide catalysts.

Authors:  Filip Kolundzic; Mohammad N Noshi; Meiliana Tjandra; Mohammad Movassaghi; Scott J Miller
Journal:  J Am Chem Soc       Date:  2011-05-23       Impact factor: 15.419

5.  A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP.

Authors:  Yukako Saito; Yuichi Yoshimura; Hideaki Wakamatsu; Hiroki Takahata
Journal:  Molecules       Date:  2013-01-16       Impact factor: 4.411

  5 in total

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