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Letter

O-Arylative Passerini Reactions

Supporting Info

Laurent El Kaim,* Marie Gizolme, and Laurence Grimaud*;

Laboratoire Chimie et procds, Ecole Nationale Suprieure de Techniques Avances, 32 Bd Victor, 75739 Paris Cedex 15, France

Org. Lett., 2006, 8 (22), pp 5021–5023

DOI: 10.1021/ol0617502

Publication Date (Web): September 27, 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.

, laurent.elkaim@ensta.fr, ; , laurence.grimaud@ensta.fr

Abstract

The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction.

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Published In Issue October 26, 2006
Received July 17, 2006

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Letter

O-Arylative Passerini Reactions

Abstract

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Stereochemical Control of the Passerini Reaction

Direct Alkylative Passerini Reaction of Aldehydes, Isocyanides, and Free Aliphatic Alcohols Catalyzed by Indium(III) Triflate

Multicomponent Reactions of Convertible Isonitriles

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