Reductive Lithiation of Alkyl 2-Thiopyridyl Ethers to Generate Optically Pure α-Alkoxylithium Reagents

Article abstract of DOI:10.1016/0040-4039(94)85008-9

Enantiomerically pure 4-lithio-2-alkyl-1,3-dioxanes, 11 and 13 were prepared by reductive lithiation of alkyl 2-thiopyridyl ether 10, which was in turn prepared by Barton radical decarboxylation of the homogenous acid.The optical activity was introduced by chirality transfer to and from the stereogenic acetal center. - Keywords - reductive lithiation; acetals; chirality transfer; thiopyridyl; radical decarboxylation.