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Literature DB >> 20684564

Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates.

Keith R Fandrick¹, Daniel R Fandrick, Joe J Gao, Jonathan T Reeves, Zhulin Tan, Wenjie Li, Jinhua J Song, Bruce Lu, Nathan K Yee, Chris H Senanayake.

Abstract

A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.

Entities: Chemical

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Year: 2010 PMID： 20684564 DOI： 10.1021/ol101301s

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

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Cited

7 in total

1. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Authors: Ping Zhang; Ian A Roundtree; James P Morken
Journal: Org Lett Date: 2012-02-29 Impact factor: 6.005

2. Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

Authors: Mihai Raducan; Rauful Alam; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2012-11-19 Impact factor: 15.336

3. Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C.

Authors: Jackson A Gartman; Uttam K Tambar
Journal: J Org Chem Date: 2021-07-21 Impact factor: 4.198

Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates.

1. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

2. Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

3. Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C.

4. A multicomponent approach for the preparation of homoallylic alcohols.

5. Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.

6. (E)-2-(1,1-Di-cyclo-hexyl-3-phenyl-all-yl)-5,5-dimethyl-1,3,2-dioxaborinane.

7. Synthesis of Rumphellaone A and Hushinone by a Gold-Catalyzed [2 + 2] Cycloaddition.