Literature DB >> 18998642

Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Hee Yeon Cho1, James P Morken.   

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. This reductive coupling furnishes an allyl boronic ester as the reaction product, a compound which was readily converted to the derived allylic alcohol by oxidative workup.

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Year:  2008        PMID： 18998642      PMCID： PMC2676113          DOI： 10.1021/ja806113v

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


  25 in total

1.  Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes.

Authors:  Irina Beletskaya; Christina Moberg
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

2.  Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling.

Authors:  Ming-Yu Ngai; Jong-Rock Kong; Michael J Krische
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

3.  Copper-catalyzed beta-Boration of alpha,beta-unsaturated carbonyl compounds: rate acceleration by alcohol additives.

Authors:  Soungyun Mun; Ji-Eon Lee; Jaesook Yun
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

4.  A highly stereoselective sequential allylic transfer reaction of diene with diboronyl reagent and aldehydes promoted by nickel catalyst.

Authors:  Chan-Mo Yu; Jinsuop Youn; Seok-Keun Yoon; Young-Tack Hong
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

5.  Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate.

Authors:  Yoshihiro Sato; Rieko Sawaki; Nozomi Saito; Miwako Mori
Journal:  J Org Chem       Date:  2002-02-08       Impact factor: 4.354

Review 6.  Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors:  Heather E Burks; James P Morken
Journal:  Chem Commun (Camb)       Date:  2007-08-22       Impact factor: 6.222

7.  Asymmetric cyclization of omega-formyl-1,3-dienes catalyzed by a zerovalent nickel complex in the presence of silanes.

Authors:  Yoshihiro Sato; Nozomi Saito; Miwako Mori
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

8.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

9.  Nickel-catalyzed beta-boration of alpha,beta-unsaturated esters and amides with bis(pinacolato)diboron.

Authors:  Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005

10.  Platinum catalysed 3,4- and 1,4-diboration of alpha,beta-unsaturated carbonyl compounds using bis-pinacolatodiboron.

Authors:  Nathan J Bell; Andrew J Cox; Neil R Cameron; John S O Evans; Todd B Marder; Marcel A Duin; Cornelis J Elsevier; Xavier Baucherel; Arran A D Tulloch; Robert P Tooze
Journal:  Chem Commun (Camb)       Date:  2004-06-30       Impact factor: 6.222
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  18 in total

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

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

2.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

3.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

4.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

5.  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
Journal:  Org Lett       Date:  2019-07-29       Impact factor: 6.005

6.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Authors:  Laura T Kliman; Scott N Mlynarski; Grace E Ferris; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-01       Impact factor: 15.336

7.  Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis.

Authors:  Kevin B Smith; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

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

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

9.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

10.  Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors:  Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-09-29       Impact factor: 15.419
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