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Literature DB >> 25340304

Copper-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes: synthesis of cyclopropylboronates.

Alejandro Parra¹, Laura Amenós, Manuel Guisán-Ceinos, Aurora López, José Luis García Ruano, Mariola Tortosa.

Abstract

A novel Cu-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes to afford nonracemic cyclopropylboronates is described. Trapping the cyclopropylcopper intermediate with electrophilic amines allows for the synthesis of cyclopropylaminoboronic esters and demonstrates the potential of the approach for the synthesis of functionalized cyclopropanes.

Entities: Chemical

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Year: 2014 PMID： 25340304 DOI： 10.1021/ja510419z

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

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Cited

20 in total

1. Diversity-Oriented Enzymatic Synthesis of Cyclopropane Building Blocks.

Authors: Bruce J Wittmann; Anders M Knight; Julie L Hofstra; Sarah E Reisman; S B Jennifer Kan; Frances H Arnold
Journal: ACS Catal Date: 2020-06-04 Impact factor: 13.084

2. Directed nucleophilic addition of phenoxides to cyclopropenes.

Authors: Pavel Yamanushkin; Michael Lu-Diaz; Andrew Edwards; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal: Org Biomol Chem Date: 2017-10-04 Impact factor: 3.876

3. Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.

Authors: Jose M Medina; Taeho Kang; Tuğçe G Erbay; Huiling Shao; Gary M Gallego; Shouliang Yang; Michelle Tran-Dubé; Paul F Richardson; Joseph Derosa; Ryan T Helsel; Ryan L Patman; Fen Wang; Christopher P Ashcroft; John F Braganza; Indrawan McAlpine; Peng Liu; Keary M Engle
Journal: ACS Catal Date: 2019-10-29 Impact factor: 13.084

4. Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Authors: Mingkai Zhang; Peilin Xu; Alex J Vendola; Christophe Allais; Anne-Marie Dechert Schmitt; Robert A Singer; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2022-06-08 Impact factor: 16.823

5. Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Authors: Vladimir Maslivetc; Colby Barrett; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal: Org Biomol Chem Date: 2018-01-03 Impact factor: 3.876

6. Ligand Conformational Flexibility Enables Enantioselective Tertiary C-B Bond Formation in the Phosphonate-Directed Catalytic Asymmetric Alkene Hydroboration.

Authors: Huiling Shao; Suman Chakrabarty; Xiaotian Qi; James M Takacs; Peng Liu
Journal: J Am Chem Soc Date: 2021-03-22 Impact factor: 15.419

Copper-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes: synthesis of cyclopropylboronates.

1. Diversity-Oriented Enzymatic Synthesis of Cyclopropane Building Blocks.

2. Directed nucleophilic addition of phenoxides to cyclopropenes.

3. Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.

4. Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

5. Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

6. Ligand Conformational Flexibility Enables Enantioselective Tertiary C-B Bond Formation in the Phosphonate-Directed Catalytic Asymmetric Alkene Hydroboration.

7. Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

8. Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.

9. Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.

Review 10. Copper mediated carbometalation reactions.