Work

Mechanistic Origin of the Stereodivergence in Decarboxylative Allylation

Year: 2010

Type: article

Abstract: A stereochemical test has been used to probe the mechanism of decarboxylative allylation. This probe suggests that the mechanism of DcA reactions can change based on the substitution pattern at the alpha-carbon of the nucleophile; however, reaction via stabilized malonate nucleophiles is the lower energy pathway. Lastly, this mechanistic proposal has predictive power and can be used to explain chemoselectivities in decarboxylative reactions that were previously confounding.

Source: Organic Letters

DOI: 10.1021/ol101042x

Authors: Kalicharan Chattopadhyay, Ranjan Jana, Victor W. Day, Justin T. Douglas, Jon A. Tunge

Institution: University of Kansas

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Center of Excellence in Chemical Methodologies and Library Development