Literature DB >> 15200298

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

Stefan Dahmen1.   

Abstract

[reaction: see text] [2.2]Paracyclophane-based ketimine ligands were evaluated as catalysts for the enantioselective addition of in situ-prepared alkynylzinc reagents to aldehydes. The initial high activity and enantioselectivity of these ligands could be improved by an additive screening. The final protocol gives chiral propargyl alcohols in up to >98% ee.

Entities:  

Year:  2004        PMID: 15200298     DOI: 10.1021/ol049596b

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


  7 in total

1.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors:  Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  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

3.  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

4.  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

5.  A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

Authors:  Jia Liu; Honglian Li; Chao Zheng; Shichao Lu; Xianru Guo; Xinming Yin; Risong Na; Bin Yu; Min Wang
Journal:  Molecules       Date:  2017-02-27       Impact factor: 4.411

6.  Highly enantioselective addition of phenylethynylzinc to aldehydes catalyzed by chiral cyclopropane-based amino alcohols.

Authors:  Bing Zheng; Zhiyuan Li; Feipeng Liu; Yanhua Wu; Junjian Shen; Qinghua Bian; Shicong Hou; Ming Wang
Journal:  Molecules       Date:  2013-12-11       Impact factor: 4.411

7.  Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.

Authors:  Sundaravel Vivek Kumar; Patrick J Guiry
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-09       Impact factor: 16.823

  7 in total

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