Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes.

Literature DB >> 12452703

A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes.

Abstract

A Cu-catalyzed method for the addition of Grignard reagents to 1-alkyl-3-hydroxymethylcyclopropenes and their MOM ethers is described. The face of addition is syn relative to the hydroxymethyl and alkoxymethyl groups. Excellent diastereoselectivity is observed for a range of alkyl, alkenyl, and alkynylmagnesium halides. The addition reactions create chiral all-carbon quaternary centers, and the cyclopropylmetals that are generated can be reacted with electrophiles to produce highly functionalized cyclopropanes.

Entities: Chemical Gene

Year: 2002 PMID： 12452703 DOI： 10.1021/ja0278234

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

Keyword Cloud
Cited

16 in total

1. Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles.

Authors: Stepan Chuprakov; Vladimir Gevorgyan
Journal: Org Lett Date: 2007-09-25 Impact factor: 6.005

2. 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

3. Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

Authors: Natasha F O'Rourke; Glenn C Micalizio
Journal: Org Lett Date: 2016-03-01 Impact factor: 6.005

4. Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift.

Authors: Xiaocong Xie; Zhe Yang; Joseph M Fox
Journal: J Org Chem Date: 2010-06-04 Impact factor: 4.354

5. 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

A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes.

1. Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles.

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

3. Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

4. Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift.

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

6. Directed carbozincation reactions of cyclopropene derivatives.

7. Highly enantio- and diastereoselective one-pot methods for the synthesis of halocyclopropyl alcohols.

Review 8. trans-Cyclooctene--a stable, voracious dienophile for bioorthogonal labeling.

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

Review 10. Copper mediated carbometalation reactions.