87763-71-1Relevant academic research and scientific papers
Stereocontrolled Synthesis of Highly Oxygenated Acyclic Systems via the Enolate Claisen Rearrangement of O-Protected Allylic Glycolates
Gould, Thomas J.,Balestra, Michael,Wittman, Mark D.,Gary, Jill A.,Rossano, Lucius T.,Kallmerten, James
, p. 3889 - 3901 (2007/10/02)
Enolate Claisen rearrangement of E- and Z-allylic glycolates yields the syn- and anti-2-alkoxy-3-alkyl 4-enoates, respectively, in good yields (60-90percent) and with high internal diastereoselectivity.Incorporation of the glycolate Claisen procedure into an iterative sequence consisting of Claisen rearrangement and homologation by addition of vinyl nucleophiles results in the efficient, stereocontrolled generation of remotely functionalized, highly oxygenated acyclic systems.This strategy is demonstrated in stereoselective syntheses of pine sawfly pheromone 42 and tocopherol side-chain intermediate 30.
Chelation Control of Enolate Geometry. Acyclic Diastereoselection via the Enolate Claisen Rearrangement
Burke, Steven D.,Fobare, William F.,Pacofsky, Gregory J.
, p. 5221 - 5228 (2007/10/02)
The Ireland-Claisen rearrangements of a variety of O-protected allylic glycolate esters are described.Vicinal diastereoselectivities ranging from 7.2:1 to >20:1 were observed, indicating that chelation control of enolate geometry is operational in the con
