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Literature DB >> 20481451

Ni-catalyzed borylative diene-aldehyde coupling: the remarkable effect of P(SiMe3)3.

Abstract

The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. In the presence of P(SiMe(3))(3), this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy(3) as the ligand. The coupling product may be subject to oxidation, which furnishes the derived 1,3-diol, or allylation with an additional aldehyde, which furnishes the derived 1,6-diol in a stereoselective fashion.

Entities: Chemical Gene

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Year: 2010 PMID： 20481451 PMCID： PMC2912217 DOI： 10.1021/ja101513d

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

18 in total

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4. Copper-catalyzed gamma-selective and stereospecific substitution reaction of allylic carbonates with diboron: efficient route to chiral allylboron compounds.

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5. Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

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2. Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates.

Authors: Natalia Cabrera-Lobera; M Teresa Quirós; William W Brennessel; Michael L Neidig; Elena Buñuel; Diego J Cárdenas
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4. Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.

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Journal: Angew Chem Int Ed Engl Date: 2014-07-15 Impact factor: 15.336

5. Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes.

Authors: Matthew G Beaver; Timothy F Jamison
Journal: Org Lett Date: 2011-06-30 Impact factor: 6.005

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7. Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

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Review 9. Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms.

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