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Literature DB >> 18393519

Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into alpha,beta-unsaturated carbonyl compounds.

Masahiro Egi¹, Yoshiko Yamaguchi, Noboru Fujiwara, Shuji Akai.

Abstract

The combination of Mo and cationic Au catalysts dramatically accelerated the rearrangement of diverse propargyl alcohols, which includes a short reaction time, mild conditions, and high product yields. A practical application to the highly challenging primary propargyl alcohols and the N-alkynyl amides is achieved.

Entities: Chemical

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Year: 2008 PMID： 18393519 DOI： 10.1021/ol800596c

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

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Cited

13 in total

Review 1. Ynamides: a modern functional group for the new millennium.

Authors: Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2010-09-08 Impact factor: 60.622

2. S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors: Andrea M Cook; Christian Wolf
Journal: Tetrahedron Lett Date: 2015-05-06 Impact factor: 2.415

3. Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors: Andrea M Cook; Christian Wolf
Journal: Chem Commun (Camb) Date: 2014-02-12 Impact factor: 6.222

4. Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors: Andrea M Cook; Christian Wolf
Journal: Angew Chem Int Ed Engl Date: 2016-01-25 Impact factor: 15.336

5. Combining Zn Ion Catalysis with Homogeneous Gold Catalysis: An Efficient Annulation Approach to N-Protected Indoles.

Authors: Yanzhao Wang; Lianzhu Liu; Liming Zhang
Journal: Chem Sci Date: 2013-02-01 Impact factor: 9.825

6. Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones.

Authors: Ya-Ping Xiao; Xin-Yuan Liu; Chi-Ming Che
Journal: Beilstein J Org Chem Date: 2011-08-11 Impact factor: 2.883

Mo-Au combo catalysis for rapid 1,3-rearrangement of propargyl alcohols into alpha,beta-unsaturated carbonyl compounds.

Review 1. Ynamides: a modern functional group for the new millennium.

2. S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

3. Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

4. Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

5. Combining Zn Ion Catalysis with Homogeneous Gold Catalysis: An Efficient Annulation Approach to N-Protected Indoles.

6. Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones.

7. Gold-catalyzed propargylic substitutions: Scope and synthetic developments.

8. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

9. Regioselective dihalohydration reactions of propargylic alcohols: gold-catalyzed and noncatalyzed reactions.

10. Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.