Literature DB >> 25734220

Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling.

Tao Liang1, Khoa D Nguyen, Wandi Zhang, Michael J Krische.   

Abstract

Chiral ruthenium(II) complexes modified by Josiphos ligands catalyze the reaction of alkynes with primary alcohols to form homoallylic alcohols with excellent control of regio-, diastereo-, and enantioselectivity. These processes represent the first examples of enantioselective carbonyl allylation using alkynes as allylmetal equivalents.

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Year:  2015        PMID： 25734220      PMCID： PMC4385519          DOI： 10.1021/jacs.5b00747

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


  34 in total

1.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

2.  Diastereo- and enantioselective iridium-catalyzed carbonyl propargylation from the alcohol or aldehyde oxidation level: 1,3-enynes as allenylmetal equivalents.

Authors:  Laina M Geary; Sang Kook Woo; Joyce C Leung; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-15       Impact factor: 15.336

3.  Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors:  Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal:  Chemistry       Date:  2011-09-27       Impact factor: 5.236

4.  Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

Authors:  Tomoya Miura; Yui Nishida; Masao Morimoto; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

5.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Authors:  Pankaj Jain; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

6.  Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

7.  Catalytic enantioselective allylboration of ketones.

Authors:  Reiko Wada; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2004-07-28       Impact factor: 15.419

8.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

Authors:  Hugo Lachance; Xiaosong Lu; Michel Gravel; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2003-08-27       Impact factor: 15.419

9.  Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry.

Authors:  Tomoya Miura; Yui Nishida; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2014-04-22       Impact factor: 15.419

10.  Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition.

Authors:  Boyoung Y Park; Khoa D Nguyen; Mani Raj Chaulagain; Venukrishnan Komanduri; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-07-30       Impact factor: 15.419
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  24 in total

1.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

2.  Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors:  Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

3.  Ruthenium-Catalyzed Asymmetric Hydrohydroxyalkylation of Butadiene: The Role of the Formyl Hydrogen Bond in Stereochemical Control.

Authors:  Matthew N Grayson; Michael J Krische; K N Houk
Journal:  J Am Chem Soc       Date:  2015-07-06       Impact factor: 15.419

4.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

Review 5.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

6.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

Review 7.  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

8.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

9.  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

10.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419
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