Tetrahedron letters

Reductive lithiation of alkyl 2-thiopyridyl ethers to generate optically pure α-alkoxylithium reagents

SD Rychnovsky, K Plzak, D Pickering

Index: Rychnovsky, Scott D.; Plzak, Kevin; Pickering, Dacia Tetrahedron Letters, 1994 , vol. 35, # 37 p. 6799 - 6802

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Citation Number: 16

Abstract

Abstract 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 homologous acid. The optical activity was introduced by chirality transfer to and from the stereogenic acetal center.