Benjamin N. Rocke, Edward L. Conn, S. Eisenbeis
Oct 10, 2012
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron Letters
Abstract
Abstract While optimizing the synthesis of pharmaceutical building block 3 [ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate], we encountered an unusual addition of an aryllithium reagent to the ketone oxygen atom of diethyl ketomalonate. Compound 3 was ultimately prepared on a large scale by a two-step sequence involving (1) annulation of a functionalized Grignard reagent with diethyl ketomalonate and (2) selective mono-reduction of a geminal diester using lithium tri- tert -butoxyaluminum hydride.