Mechanistic investigation of the enantioselective intramolecular stetter reaction: Proton transfer is the first irreversible step

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1742-1745

  Moore, Jennifer L ^a,b   Silvestri, Anthony P ^a   De Alaniz, Javier Read ^a,c   Dirocco, Daniel A ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b PEPPERDINE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM;

ALDEHYDES; KINETICS; MOLECULAR STRUCTURE; PROTONS; STEREOISOMERISM;

EID: 79953171934     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200256a     Document Type: Article

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39. See Supporting Information for the details of the kinetic experiments and the corresponding graphs.
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44. 4 is completely insoluble under these conditions.
45. That substrate 12 still undergoes reaction means that there must be another mechanism available for proton transfer, presumably either via Hypothesis II above or involving another molecule of catalyst or intermediate, as argued by Yates (see ref 18).