Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis

US6794534B2 · kind B2 · utility

Assignee

• CALIFORNIA INSTITUTE OF TECHNOLOGY · US

Inventors

• Robert H. Grubbs · La Cañada Flintridge, US
• Arnab K. Chatterjee · Encinitas, US
• John P. Morgan · Cheektowaga, US
• Matthias Scholl · Arcadia, US
• Tae Lim Choi · Seongnam-si, KR

Key dates

• Filing date: Jun 25, 2001
• Grant date: Sep 21, 2004
• Expiry date: Jun 25, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D413/12
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention is directed to the cross-metathesis and ring-closing metathesis reactions between geminal disubstituted olefins and terminal olefins, wherein the reaction employs a Ruthenium or Osmium metal carbene complex. Specifically, the invention relates to the synthesis of &agr;-functionalized or unfunctionalized olefins via intermolecular cross-metathesis and intramolecular ring-closing metathesis using a ruthenium alkylidene complex. The catalysts preferably used in the invention are of the general formula wherein:M is ruthenium or osmium;X and X1 are each independently an anionic ligand;L is a neutral electron donor ligand; and,R, R1R6, R7, R8, and R9 are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.