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Literature DB >> 33742749

Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes.

Yair Cohen¹, André U Augustin¹, Laura Levy¹, Peter G Jones², Daniel B Werz³, Ilan Marek¹.

Abstract

Despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters, the regio- and diastereoselective copper-catalyzed carbomagnesiation reaction of cyclopropenes provides an easy and efficient access to these novel persubstituted cyclopropyl cores with a complete regio- and diastereoselectivity.

Entities: Chemical Gene

Keywords: carbon quaternary stereocenters; copper-catalyzed carbomagnesiation; diastereoselectivity; persubstituted cyclopropanes

Year: 2021 PMID： 33742749 DOI： 10.1002/anie.202102509

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

8 in total

1. Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives.

Authors: Anthony Cohen; Alexander Kaushansky; Ilan Marek
Journal: JACS Au Date: 2022-03-05

2. Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

Authors: Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek
Journal: J Am Chem Soc Date: 2022-04-12 Impact factor: 16.383

3. Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.

Authors: Xu Chen; Ilan Marek
Journal: Angew Chem Int Ed Engl Date: 2022-05-11 Impact factor: 16.823

4. Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives.

Authors: Yogesh Siddaraju; Juliette Sabbatani; Anthony Cohen; Ilan Marek
Journal: Angew Chem Int Ed Engl Date: 2022-05-20 Impact factor: 16.823

5. Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems.

Authors: André U Augustin; Sergio Di Silvio; Ilan Marek
Journal: J Am Chem Soc Date: 2022-08-30 Impact factor: 16.383

Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes.

1. Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives.

2. Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

3. Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.

4. Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives.

5. Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems.

6. Regio- and Diastereoselective Carbometalation Reaction of Cyclopropenes.

7. Stereoselective Synthesis of Polysubstituted Spiropentanes.

8. Rh(II)-Catalyzed Alkynylcyclopropanation of Alkenes by Decarbenation of Alkynylcycloheptatrienes.