Literature DB >> 22360547

Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

Chao Jiang1, Dustin J Covell, Antonia F Stepan, Mark S Plummer, M Christina White.   

Abstract

Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under n class="Chemical">Pd(II)/sulfoxide-catalysis that furnishes a wide range of α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.

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Year:  2012        PMID: 22360547      PMCID: PMC4104998          DOI: 10.1021/ol300063t

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


  56 in total

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2.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

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Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

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Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

5.  Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction.

Authors:  Erik M Stang; M Christina White
Journal:  J Am Chem Soc       Date:  2011-09-01       Impact factor: 15.419

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7.  Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors:  Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

8.  Synthesis of complex allylic esters via C-H oxidation vs C-C bond formation.

Authors:  Nicolaas A Vermeulen; Jared H Delcamp; M Christina White
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

9.  Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating.

Authors:  Jonas Lindh; Per-Anders Enquist; Ake Pilotti; Peter Nilsson; Mats Larhed
Journal:  J Org Chem       Date:  2007-09-21       Impact factor: 4.354

10.  Catalytic allylic C-H acetoxylation and benzoyloxylation via suggested (eta(3)-allyl)palladium(IV) intermediates.

Authors:  Lukasz T Pilarski; Nicklas Selander; Dietrich Böse; Kálmán J Szabó
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

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  2 in total

1.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236

2.  A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

Authors:  Dustin J Covell; M Christina White
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

  2 in total

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