Literature DB >> 16390095

Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Barry M Trost1, Andrew H Weiss, Axel Jacobi von Wangelin.   

Abstract

Our recent development of a proline-derived bimetallic catalyst has led to a number of efficient, catalytic, enantioselective transformations. Herein, we report a practical and general alkynylation of aromatic and alpha,beta-unsaturated aldehydes using our zinc catalyst system.

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Year:  2006        PMID： 16390095      PMCID： PMC2596613          DOI： 10.1021/ja054871q

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


  16 in total

1.  Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts.

Authors:  B M Trost; E R Silcoff; H Ito
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

2.  Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.

Authors:  Barry M Trost; Vince S C Yeh; Hisanako Ito; Nadine Bremeyer
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005

3.  A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction.

Authors:  Barry M Trost; Vince S C Yeh
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-01       Impact factor: 15.336

4.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction.

Authors:  Barry M Trost; Alec Fettes; Brock T Shireman
Journal:  J Am Chem Soc       Date:  2004-03-10       Impact factor: 15.419

Review 5.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

6.  Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.

Authors:  Barry M Trost; Seunghoon Shin; Joseph A Sclafani
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

7.  BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes.

Authors:  David Moore; Lin Pu
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

8.  Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a camphorsulfonamide ligand.

Authors:  Zhaoqing Xu; Chao Chen; Jiangke Xu; Mingbo Miao; Wenjin Yan; Rui Wang
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

9.  Enantioselective alkynylation of aldehydes catalyzed by [2.2]paracyclophane-based ligands.

Authors:  Stefan Dahmen
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

10.  Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.

Authors:  Ge Gao; Ru-Gang Xie; Lin Pu
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-16       Impact factor: 11.205
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  30 in total

1.  Asymmetric synthesis of D-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354

2.  Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

3.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

4.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

5.  Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes.

Authors:  Barry M Trost; Christopher A Kalnmals
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

6.  Total synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle; Daniel Hund
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

7.  Cyclic Acetal Formation Between 2-Pyridinecarboxaldehyde and gamma-Hydroxy-alpha,beta-Acetylenic Esters.

Authors:  Sami Osman; Kazunori Koide
Journal:  Tetrahedron Lett       Date:  2008-11-10       Impact factor: 2.415

8.  Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

Authors:  Barry M Trost; Alicia C Gutierrez; Robert C Livingston
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

9.  Exploiting orthogonally reactive functionality: synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

10.  1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes.

Authors:  Qin Wang; Shan-Yong Chen; Xiao-Qi Yu; Lin Pu
Journal:  Tetrahedron       Date:  2007-05-21       Impact factor: 2.457
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