Literature DB >> 17971951

Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes.

Ryan M Moslin1, Karen Miller-Moslin, Timothy F Jamison.   

Abstract

Nickel-catalysed reductive coupling reactions of alkynes have emerged as powerful synthetic tools for the selective preparation of functionalized alkenes. One of the greatest challenges associated with these transformations is control of regioselectivity. Recent work from our laboratory has provided an improved understanding of several of the factors governing regioselectivity in these reactions, and related studies have revealed that the reaction mechanism can differ substantially depending on the ligand employed. A discussion of stereoselective transformations and novel applications of nickel catalysis in coupling reactions of alkynes is also included.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17971951      PMCID： PMC3130994          DOI： 10.1039/b707737h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  35 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Asymmetric Ni(II)/Cr(II)-mediated coupling reaction: catalytic process.

Authors:  Hyeong-Wook Choi; Katsumasa Nakajima; Damtew Demeke; Fu-An Kang; Hyuk-Sang Jun; Zhao-Kui Wan; Yoshito Kishi
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

3.  Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group--direct access to enantiomerically pure primary allylic amines.

Authors:  Sejal J Patel; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

4.  Mechanistic implications of nickel-catalyzed reductive coupling of aldehydes and chiral 1,6-enynes.

Authors:  Ryan M Moslin; Timothy F Jamison
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

5.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Authors: 
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

6.  Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors:  Kanicha Sa-ei; John Montgomery
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

7.  Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes.

Authors:  Karen M Miller; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  Novel applications of alkenyl zirconocenes.

Authors:  Peter Wipf; Christopher Kendall
Journal:  Chemistry       Date:  2002-04-15       Impact factor: 5.236

9.  A comparative analysis of the total syntheses of the amphidinolide T natural products.

Authors:  Elizabeth A Colby; Timothy F Jamison
Journal:  Org Biomol Chem       Date:  2005-07-01       Impact factor: 3.876

10.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419
View more
  30 in total

1.  Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

Authors:  Santiago Cañellas; John Montgomery; Miquel À Pericàs
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  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

Review 3.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Vanessa M Williams; John F Bower; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Mechanisms for the synthesis of conjugated enynes from diphenylacetylene and trimethylsilylacetylene catalyzed by a nickel(0) complex: DFT study of ligand-controlled selectivity.

Authors:  Cheng Huang; Rongxing He; Wei Shen; Ming Li
Journal:  J Mol Model       Date:  2015-05-03       Impact factor: 1.810

6.  Mechanism and origins of regio- and enantioselectivities in RhI-catalyzed hydrogenative couplings of 1,3-diynes and activated carbonyl partners: intervention of a cumulene intermediate.

Authors:  Peng Liu; Michael J Krische; Kendall N Houk
Journal:  Chemistry       Date:  2011-03-01       Impact factor: 5.236

7.  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

8.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

9.  Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs.

Authors:  Abdur-Rafay Shareef; David H Sherman; John Montgomery
Journal:  Chem Sci       Date:  2011-12-06       Impact factor: 9.825

10.  Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

Authors:  Dexi Yang; Justin K Belardi; Glenn C Micalizio
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.