Literature DB >> 23721207

Regioselective ruthenium catalyzed hydrohydroxyalkylation of dienes with 3-hydroxy-2-oxindoles: prenylation, geranylation, and beyond.

Te-Yu Chen1, Michael J Krische.   

Abstract

The direct conversion of secondary to tertiary alcohols via ruthenium(0) catalyzed C-C coupling of substituted 3-hydroxy-2-oxindoles with various dienes is described. Coupling occurs in a completely regioselective manner in the absence of stoichiometric byproducts.

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Year:  2013        PMID： 23721207      PMCID： PMC3800700          DOI： 10.1021/ol401184k

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


  25 in total

1.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  A New catalytic C[bond]C bond-forming hydrogenation: reductive coupling of dienes and glyoxals under catalytic hydrogenation conditions.

Authors:  Hye-Young Jang; Ryan R Huddleston; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

3.  Synthesis of α-amino acid amides: ruthenium-catalyzed amination of α-hydroxy amides.

Authors:  Min Zhang; Sebastian Imm; Sebastian Bähn; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-10       Impact factor: 15.336

4.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

5.  Rh-catalyzed reductive coupling reaction of aldehydes with conjugated dienes promoted by triethylborane.

Authors:  Masanari Kimura; Daisuke Nojiri; Masahiro Fukushima; Shuichi Oi; Yusuke Sonoda; Yoshio Inoue
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

6.  Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: highly enantioselective synthesis of chiral bishomoallylic alcohols.

Authors:  Yun Yang; Shou-Fei Zhu; Hai-Feng Duan; Chang-Yue Zhou; Li-Xin Wang; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-02-02       Impact factor: 15.419

7.  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

8.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

9.  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

10.  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
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  17 in total

1.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

2.  A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

3.  Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Org Chem       Date:  2016-09-08       Impact factor: 4.354

Review 4.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

5.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

6.  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

7.  Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: isolation and reversible formation of the putative metallacycle intermediate.

Authors:  Boyoung Y Park; T Patrick Montgomery; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-10-24       Impact factor: 15.419

Review 8.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

Review 9.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336

10.  Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition.

Authors:  Zachary A Kasun; Laina M Geary; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2014-07-18       Impact factor: 6.222
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