Literature DB >> 18027963

Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Jacqueline D Hicks1, Chan Woo Huh, Ashley D Legg, William R Roush.   

Abstract

Treatment of unsaturated 1,5-diols 2 with TES-Cl (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with >95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

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Year:  2007        PMID： 18027963      PMCID： PMC2504016          DOI： 10.1021/ol702588h

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


  15 in total

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3.  Total synthesis of (+)-13-deoxytedanolide.

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Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

5.  Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors:  Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

6.  Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS.

Authors:  Jong Hyun Cho; Dale L Bernard; Robert W Sidwell; Earl R Kern; Chung K Chu
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Authors:  B J Banks; B F Bishop; N A Evans; S P Gibson; A C Goudie; K A Gration; M S Pacey; D A Perry; M J Witty
Journal:  Bioorg Med Chem       Date:  2000-08       Impact factor: 3.641

9.  How constant are Ritchie's "constant selectivity relationships"? A general reactivity scale for n-, pi-, and sigma-nucleophiles.

Authors:  Shinya Minegishi; Herbert Mayr
Journal:  J Am Chem Soc       Date:  2003-01-08       Impact factor: 15.419

10.  Synthesis of 2,6-trans-disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols.

Authors:  Eric M Flamme; William R Roush
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883
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  2 in total

1.  Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide.

Authors:  Joshua R Dunetz; Lisa D Julian; Jason S Newcom; William R Roush
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

2.  Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.

Authors:  Fangzheng Li; William R Roush
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005
  2 in total

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