Literature DB >> 10891259

Synthesis of beta-hydroxy ketones and vinylsilanes from homopropargylic alcohols by intramolecular hydrosilation

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Abstract

Catalytic intramolecular hydrosilation of nonracemic homopropargylic alcohols affords the corresponding five-membered cyclic siloxanes regiospecifically. Oxidation or alkylmetal addition converts these intermediates into beta-hydroxy ketones or vinylsilanes under mild conditions.

Entities:  

Year:  2000        PMID: 10891259     DOI: 10.1021/ol0061182

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


  7 in total

1.  Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors:  Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-10       Impact factor: 15.336

2.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

3.  An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality.

Authors:  Barry M Trost; Zachary T Ball; Kai M Laemmerhold
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

4.  Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.

Authors:  Barry M Trost; Zachary T Ball
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

5.  Total synthesis of neopeltolide and analogs.

Authors:  Yubo Cui; Wangyang Tu; Paul E Floreancig
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

6.  Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N.

Authors:  Barry M Trost; Jullien Rey
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

7.  Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Authors:  Wangyang Tu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

  7 in total

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