Literature DB >> 21905748

Stereoselective borylative ketone-diene coupling.

Hee Yeon Cho1, Zhiyong Yu, James P Morken.   

Abstract

In the presence of catalytic Ni(cod)(2) and P(t-Bu)(3), ketones, dienes, and B(2)(pin)(2) undergo a stereoselective multicomponent coupling reaction. Upon oxidation, the reaction furnishes 1,3-diols as the major reaction product.
© 2011 American Chemical Society

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Year:  2011        PMID： 21905748      PMCID： PMC3195430          DOI： 10.1021/ol202138v

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


  27 in total

1.  Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]: synergy between a strong sigma donor and a strong pi acceptor.

Authors:  Chun-Yu Ho; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes.

Authors:  Masanari Kimura; Akihiro Ezoe; Masahiko Mori; Keisuke Iwata; Yoshinao Tamaru
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

3.  Nickel-catalyzed indium(I)-mediated double addition of aldehydes to 1,3-dienes.

Authors:  Tsunehisa Hirashita; Shinya Kambe; Hiromitsu Tsuji; Shuki Araki
Journal:  Chem Commun (Camb)       Date:  2006-05-09       Impact factor: 6.222

4.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

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

6.  Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-11-15       Impact factor: 15.336

Review 7.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

8.  Origins of regioselectivity and alkene-directing effects in nickel-catalyzed reductive couplings of alkynes and aldehydes.

Authors:  Peng Liu; Patrick McCarren; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  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

10.  Nickel-catalyzed homoallylation reaction of aldehydes with 1,3-dienes: stereochemical and mechanistic studies.

Authors:  Teck-Peng Loh; Hong-Yan Song; Yan Zhou
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005
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  7 in total

1.  Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

Authors:  Emma L McInturff; Khoa D Nguyen; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

2.  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

3.  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

Review 4.  Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms.

Authors:  Hee Yeon Cho; James P Morken
Journal:  Chem Soc Rev       Date:  2014-04-16       Impact factor: 54.564

Review 5.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

6.  Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.

Authors:  Alexander Fawcett; Dominik Nitsch; Muhammad Ali; Joseph M Bateman; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-26       Impact factor: 15.336

7.  Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.

Authors:  Jian-Jun Feng; Yan Xu; Martin Oestreich
Journal:  Chem Sci       Date:  2019-08-20       Impact factor: 9.825
  7 in total

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