Convergent Evolution of Diastereomeric Mixtures of 5-Methoxy-pentylzirconocenes toward Trans-1,2-substituted Cyclopentanes.


Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
05 02 2021
Historique:
pubmed: 14 1 2021
medline: 14 1 2021
entrez: 13 1 2021
Statut: ppublish

Résumé

The access to 1,2- and 1,1,2-substituted trans cyclopentanes via a sequential hydrozirconation/TMSOTf-mediated cyclization applied to 5-methoxypent-1-enes is presented. Involving a transient carbocation, the reaction was shown to be diastereo-convergent. Possibly performed in a nonracemic version, the reaction proved compatible with a range of functional groups affording a large panel of cyclopentanes.

Identifiants

pubmed: 33439667
doi: 10.1021/acs.orglett.0c03998
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

772-776

Auteurs

Aurélien Coelho (A)

Institut de Chimie Moléculaire de Reims-CNRS (UMR 7312) and Université de Reims Champagne Ardenne, 51687 Reims Cedex 2, France.

Carine Machado-Rodrigues (C)

Institut de Chimie Moléculaire de Reims-CNRS (UMR 7312) and Université de Reims Champagne Ardenne, 51687 Reims Cedex 2, France.

Jean-Bernard Behr (JB)

Institut de Chimie Moléculaire de Reims-CNRS (UMR 7312) and Université de Reims Champagne Ardenne, 51687 Reims Cedex 2, France.

Jean-Luc Vasse (JL)

Institut de Chimie Moléculaire de Reims-CNRS (UMR 7312) and Université de Reims Champagne Ardenne, 51687 Reims Cedex 2, France.

Classifications MeSH