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Transition-Metal-Mediated Cascade Reactions: C,C-Dicyclopropylmethylamines by Way of Double C,C-σ-Bond Insertion into Bicyclobutanes

Supporting Info

Peter Wipf,* Corey R. J. Stephenson, and Kazuo Okumura

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

J. Am. Chem. Soc., 2003, 125 (48), pp 14694–14695

DOI: 10.1021/ja038623a

Publication Date (Web): November 6, 2003

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

, pwipf@pitt.edu

Abstract

The organometallic multicomponent reaction of alkenyl zirconocene, alkynyl imine, and zinc carbenoid in the presence of dimethylzinc leads to novel C,C-dicyclopropylmethylamines. The formation of intermediate bicyclo[1.1.0]butanes represents the first synthetically useful example of a double C,C-σ-bond insertion, and the increase in structural complexity from starting materials is highlighted by the formation of nine new C,C-bonds in the final product.

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Published In Issue December 03, 2003
Received September 19, 2003

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Communication

Transition-Metal-Mediated Cascade Reactions: C,C-Dicyclopropylmethylamines by Way of Double C,C-σ-Bond Insertion into Bicyclobutanes

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

The Tandem Cope-Type Hydroamination/[2,3]-Rearrangement Sequence: A Strategy to Favor the Formation of Intermolecular Hydroamination Products and Enable Difficult Cyclizations

A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

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