217969-74-9Relevant academic research and scientific papers
Highly stereoselective radical cyclization of haloacetals controlled by the acetal center
Villar, Felix,Kolly-Kovac, Tanja,Equey, Olivier,Renaud, Philippe
, p. 1566 - 1577 (2007/10/03)
A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and γ-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)-eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.
Diastereoselective radical cyclization of bromoacetals (Ueno-Stork reaction) controlled by the acetal center
Villar, Felix,Renaud, Philippe
, p. 8655 - 8658 (2007/10/03)
The stereochemistry of the 5-exo-trig cyclization of bromoacetals (Ueno- Stork cyclization) can be controlled from the stereogenic acetal center. High stereoselectivities have been observed for the formation of 4-substituted tetrahydrofurans. Preparation
