123186-15-2Relevant academic research and scientific papers
Heterocycle synthesis based on allylic alcohol transposition using traceless trapping groups
Xie, Youwei,Floreancig, Paul E.
supporting information, p. 4926 - 4929 (2014/05/20)
Allylic alcohols undergo transposition reactions in the presence of Re 2O7 whereby the equilibrium can be dictated by trapping one isomer with a pendent electrophile. Additional ionization can occur when the trapping group is an aldehyde or ketone, thus leading to cyclic oxocarbenium ion formation. Terminating the process through bimolecular nucleophilic addition into the intermediate provides a versatile method for the synthesis of diverse oxygen-containing heterocycles. Understanding the relative rates of the steps in the sequence leads to the design of reactions which create multiple stereocenters with good to excellent levels of control.
Preparation of Seven-Membered-Ring Cyclic Ethers and 3-Alkylidenetetrahydropyrans from the Cyclization of Oxonium Cations Derived from Unsubstituted and Silicon-Containing 4-Alken-1-ols
Castaneda, Armando,Kucera, David J.,Overman, Larry E.
, p. 5695 - 5707 (2007/10/02)
Lewis acid promoted cyclization of mixed acetals derived from 4-alken-1-ols provides direct access to seven- or six-membered cyclic ethers.Ring size is determined primarily by the electronic bias of the alkene participant.Of particular significance are (a
