Work

Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition

Year: 2012

Type: article

Abstract: We have developed two different types of tandem reactions for the synthesis of highly functionalized cyclohexenones from cyclopropyl substituted propargyl esters. Both reactions were initiated by rhodium-catalyzed Saucy-Marbet 1,3-acyloxy migration. The resulting cyclopropyl substituted allenes derived from acyloxy migration then underwent [5 + 1] cycloaddition with CO. The acyloxy group not only eased the access to allene intermediates but also provided a handle for further selective functionalizations.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo300973r

Authors: Dongxu Shu, Xiaoxun Li, Min Zhang, Patrick J. Robichaux, Ilia A. Guzei, Weiping Tang

Institution: University of Wisconsin–Madison

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Award: Development of Cyclopropyl Metal Carbene Based Methods for Organic Synthesis