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Literature DB >> 21250749

Enantioselective palladium-catalyzed carbozincation of cyclopropenes.

Katja Krämer¹, Paul Leong, Mark Lautens.

Abstract

A highly enantioselective palladium-catalyzed carbozincation of cyclopropenes has been developed. The intermediate cyclopropylzinc species, after transmetalation with copper, were trapped with various electrophiles. This one-pot procedure furnished functionalizied cyclopropenes with excellent diastereo- and enantioselectivity.

Entities: Chemical

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Year: 2011 PMID： 21250749 DOI： 10.1021/ol1029904

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

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Cited

14 in total

1. Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

Authors: Matthew D Hassink; Joseph M Fox
Journal: Synthesis (Stuttg) Date: 2012 Impact factor: 3.157

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. Metalloradical Activation of In Situ-Generated α-Alkynyldiazomethanes for Asymmetric Radical Cyclopropanation of Alkenes.

Authors: Jing Ke; Wan-Chen Cindy Lee; Xiaoxu Wang; Yong Wang; Xin Wen; X Peter Zhang
Journal: J Am Chem Soc Date: 2022-01-31 Impact factor: 16.383

4. Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors: Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal: J Org Chem Date: 2012-10-19 Impact factor: 4.354

Enantioselective palladium-catalyzed carbozincation of cyclopropenes.

1. Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

2. Directed nucleophilic addition of phenoxides to cyclopropenes.

3. Metalloradical Activation of In Situ-Generated α-Alkynyldiazomethanes for Asymmetric Radical Cyclopropanation of Alkenes.

4. Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

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

6. Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.

7. Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes.

8. Diastereo- and enantioselective preparation of cyclopropanol derivatives.

9. Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation.

Review 10. Copper mediated carbometalation reactions.