Literature DB >> 17020284

Stereochemical control in the reduction of 2-chromanols.

Kelin Li1, Kumar Vanka, Ward H Thompson, Jon A Tunge.   

Abstract

[reaction: see text] Reduction of C5-substituted 2-hydroxychromans selectively provides 2,4-cis-chromans using large silane reductants and 2,4-trans-chromans using the smaller silane PhSiH(3). The stereochemical outcome has been rationalized on the basis of a Curtin-Hammett kinetic situation arising from hydride delivery to two different conformations of an intermediate oxocarbenium ion. This method provides a powerful way to control the relative stereochemistry of these substructures which are prevalent in bioactive natural products.

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Year:  2006        PMID： 17020284      PMCID： PMC2538801          DOI： 10.1021/ol061727g

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


  9 in total

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5.  Reference scales for the characterization of cationic electrophiles and neutral nucleophiles.

Authors:  H Mayr; T Bug; M F Gotta; N Hering; B Irrgang; B Janker; B Kempf; R Loos; A R Ofial; G Remennikov; H Schimmel
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

6.  Trifluoroacetic acid-mediated hydroarylation: synthesis of dihydrocoumarins and dihydroquinolones.

Authors:  Kelin Li; Lindsay N Foresee; Jon A Tunge
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

7.  (+)-Myristinin A, a naturally occurring DNA polymerase beta inhibitor and potent DNA-damaging agent.

Authors:  David J Maloney; Jing-Zhen Deng; Shelley R Starck; Zhijie Gao; Sidney M Hecht
Journal:  J Am Chem Soc       Date:  2005-03-30       Impact factor: 15.419

8.  Structural evidence that alkoxy substituents adopt electronically preferred pseudoaxial orientations in six-membered ring dioxocarbenium ions.

Authors:  Stephen Chamberland; Joseph W Ziller; K A Woerpel
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

9.  Pi-nucleophilicity in carbon-carbon bond-forming reactions.

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Journal:  Acc Chem Res       Date:  2003-01       Impact factor: 22.384
  9 in total
  2 in total

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2.  Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Authors:  Zhenyu Yang; Ying He; F Dean Toste
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  2 in total

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