333335-38-9Relevant academic research and scientific papers
Enantioselective synthesis of a tetrasubstituted oxocane via a double diastereoselective hetero Diels-Alder reaction
Martín,Afonso,Galindo,Palenzuela
, p. 117 - 119 (2007/10/03)
A procedure for the enantioselective preparation of tetra-substituted medium sized cyclic ethers is presented. An oxocane is prepared by a sequence which involves a double diastereoselective hetero Diels-Alder reaction between a chiral aldehyde and a diene bearing an allylic chiral centre. The cycloadduct is transformed into a linear ether which is then converted to the cyclic ether by a highly regioselective intramolecular alkylation of a lithiosulfone with an epoxide. The sense of induction of the chiral centre on the diene is discussed.
