Literature DB >> 27321353

C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Tao Liang1, Sang Kook Woo1, Michael J Krische2.   

Abstract

The canonical SN 2 behavior displayed by alcohols and activated alkyl halides in basic media (O-alkylation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; hydrogenation; reaction mechanisms; rhodium; synthetic methods

Mesh：

Substances：

Year:  2016        PMID： 27321353      PMCID： PMC4965293          DOI： 10.1002/anie.201603575

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  41 in total

1.  Stereoselective synthesis of stereotriad subunits of polyketides through additions of nonracemic allenylsilanes to (R)- and (S)-2-methyl-3-oxygenated propanals

Authors: 
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

2.  Lewis base activation of Lewis acids: catalytic enantioselective allylation and propargylation of aldehydes.

Authors:  S E Denmark; T Wynn
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

3.  Studies on catalytic asymmetric Nozaki-Hiyama propargylation.

Authors:  Masahiro Inoue; Masahisa Nakada
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

4.  Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes.

Authors:  Chunqiu Lai; John A Soderquist
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

5.  Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones.

Authors:  Alexey B Zaitsev; Hans Adolfsson
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

6.  Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex.

Authors:  D A Evans; Z K Sweeney; T Rovis; J S Tedrow
Journal:  J Am Chem Soc       Date:  2001-12-05       Impact factor: 15.419

7.  B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.

Authors:  Eliud Hernandez; Carlos H Burgos; Eyleen Alicea; John A Soderquist
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

8.  First direct structural comparison of complexes of the same metal fragment to ketenes in both C,C- and C,O-bonding modes.

Authors:  D B Grotjahn; L S Collins; M Wolpert; G A Bikzhanova; H C Lo; D Combs; J L Hubbard
Journal:  J Am Chem Soc       Date:  2001-08-29       Impact factor: 15.419

9.  Stereocontrolled synthesis of (-)-macrolactin A.

Authors:  Joseph P Marino; Michael S McClure; David P Holub; João V Comasseto; Fabío C Tucci
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

10.  Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide.

Authors:  Moloy Banerjee; Sujit Roy
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005
View more
  5 in total

1.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

2.  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

3.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

4.  Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.

Authors:  Jian Zhao; Sybrand J T Jonker; Denise N Meyer; Göran Schulz; C Duc Tran; Lars Eriksson; Kálmán J Szabó
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

5.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.