82343-65-5Relevant academic research and scientific papers
Reactivity of Enol Carbonates with Ozone
Silvestri, Michael G.,Hanson, M. Paul,Pavlovich, James G.,Studen, Luisa F.,DeClue, Michael S.,DeGraffenreid, Michael R.,Amos, Christopher D.
, p. 6597 - 6602 (2007/10/03)
Several dienes of varying steric bulk containing an enol carbonate have been synthesized and reacted selectively with ozone at the isolated double bonds. Rate measurements have been made for ozonolysis in a series of substituted cyclohexenes to demonstrate the unusually slow reactivity of the enol carbonate. Proton and carbon NMR chemical shifts have been presented to show that the enol carbonate is not particularly electron deficient in its double bond. Calculation of partial charges from the Mulliken population analysis shows good correlation with the NMR data. The results suggest a carbonate association with ozone that slows the rate of carbon-carbon bond cleavage.
A Stereospecific 2 + 2 + 2 Annulation
Danishefsky, Samuel,Chackalamannil, Samuel,Silvestri, Michael,Springer, James
, p. 3615 - 3616 (2007/10/02)
A mew strategy for multiple annulation involving sequential Michael and Aldol reactions is described.
ENOL CARBONATES: WEAKLY NUCLEOPHILIC PRECURSORS OF SITE-SPECIFIC ENOLATES
Danishefsky, Samuel,Kahn, Michael,Silvestri, Michael
, p. 703 - 706 (2007/10/02)
Examples of trapping of site-specific enolates by enol methoxycarbonylation are described.Selective operations at a remote double bond in the presence of the enol carbonate functionality have been realized.Site-specific enolates can be retrieved from the
