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Wolfe JP. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett. 2006;2007(4):571-582doi: 10.1002/ejoc.200600767.
Wolfe, J. P. (2006). Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett : accounts and rapid communications in synthetic organic chemistry, 2007(4), 571-582. https://doi.org/10.1002/ejoc.200600767
Wolfe, John P. "Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions." Synlett : accounts and rapid communications in synthetic organic chemistry vol. 2007,4 (2006): 571-582. doi: https://doi.org/10.1002/ejoc.200600767
Wolfe JP. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett. 2006 Nov 13;2007(4):571-582. doi: 10.1002/ejoc.200600767. PMID: 19183704; PMCID: PMC2633094.
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Synlett. 2006 Nov 13;2007(4):571-582. doi: 10.1002/ejoc.200600767.

Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Synlett : accounts and rapid communications in synthetic organic chemistry

John P Wolfe

Affiliations

  1. University of Michigan, Department of Chemistry, 930 N. University Avenue, Ann Arbor, Michigan, 48109-1055.

PMID: 19183704 PMCID: PMC2633094 DOI: 10.1002/ejoc.200600767

Abstract

The development of Pd-catalyzed carboetherification and carboamination reactions between aryl/alkenyl halides and alkenes bearing pendant heteroatoms is described. These transformations effect the stereoselective construction of useful heterocycles such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, isoxazolidines, and piperazines. The scope, limitations, and applications of these reactions are presented, and current stereochemical models are described. The mechanism of product formation, which involves an unusual intramolecular syn-insertion of an alkene into a Pd-Heteroatom bond is also discussed in detail.

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