ChemInform Abstract: Stereoselective Synthesis of Heterocyclic Zinc Reagents via a Nickel- Catalyzed Radical Cyclization.

✍ Scribed by A. VAUPEL; P. KNOCHEL

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199706100

✦ Synopsis

Stereoselective Synthesis of Heterocyclic Zinc Reagents via a Nickel-Catalyzed Radical Cyclization.

-Starting from iodides such as (I), (VI), and (X) or bromides such as ( XIII) and (XVI) a convenient method for the preparation of substituted furans is presented. In this one-pot procedure the intermediately formed heterocyclic zinc compound reacts with different kinds of electrophiles. The preparations of the cyclization precursors are described. The usefulness of this methodology is shown by the synthesis of the lactone (XVIII), which is a known intermediate in the enantioselective synthesis of (-)-methylenolactocine.