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

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

Source and publish data:

Tetrahedron Letters p. 6799 - 6802 (1994)

Update date:2022-08-04

Topics:

Authors:

Rychnovsky, Scott D.

Plzak, Kevin

Pickering, Dacia

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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.

Full text of DOI:10.1016/0040-4039(94)85008-9

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