Synthesis of functionalized macrocycles by ring closing metathesis

US5936100A · kind A · utility

Assignee

• Studiengesellschaft Kohle gGmbH · DE

Inventors

• Alois Fürstner · Neheim, DE
• Klaus Langemann · Worms, DE
• Nicole Kindler · Mülheim an der Ruhr, DE

Key dates

• Filing date: Dec 16, 1996
• Grant date: Aug 10, 1999
• Expiry date: Dec 16, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D321/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention concerns an improved process for the preparation of macrocyclic products with 12 or more ring atoms containing one or more polar functional groups on the ring and/or one or more heteroatoms within the ring by ring closing metathesis (RCM) of suitably substituted diene precursors even if the substrates are devoid of any kind of conformational preorganization. Metal carbene complexes of Ru, Mo, W, Re, Os, which are tolerant towards the respective functional group and can either be isolated or prepared in situ are used as catalysts or catalyst precursors. Preferred catalysts or catalyst precursors are ruthenium complexes of the general type XX.sub.1 LL.sub.1 Ru.dbd.CRR.sub.1, wherein X, X.sub.1 =halogen, L, L.sub.1 =trialkylphosphine, R, R1=H, Ph, CH.dbd.CPh.sub.2 denote the most preferred embodiment. The process can be applied to the synthesis of olfactory compounds, perfumary ingredients, pheromones, crown ethers, antibiotics and pharmaceuticals for human and veterinary medicine.