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Letter

Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem Cross-Metathesis/Allylic Alcohol Isomerization

Supporting Info

David Finnegan, Benjamin A. Seigal, and Marc L. Snapper*

Department of Chemistry, Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467

Org. Lett., 2006, 8 (12), pp 2603–2606

DOI: 10.1021/ol060918g

Publication Date (Web): May 17, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, marc.snapper@bc.edu

Abstract

Grubbs' 2nd generation and Hoveyda−Grubbs' ruthenium alkylidenes are shown to be effective catalysts for cross-metatheses of allylic alcohols with cyclic and acyclic olefins, as well as isomerization of the resulting allylic alcohols to alkyl ketones. The net result of this new tandem methodology is a single-flask process that provides highly functionalized, ketone-containing products from simple allylic alcohol precursors.

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Published In Issue June 08, 2006
Received April 14, 2006

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Letter

Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem Cross-Metathesis/Allylic Alcohol Isomerization

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

A Short and Efficient Synthesis of (−)-7-Methylomuralide, a Potent Proteasome Inhibitor

Enantioselective Total Synthesis of (−)-Napyradiomycin A1 via Asymmetric Chlorination of an Isolated Olefin

Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation of Conjugated Dienoic Esters from Terminal Olefins

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