Selective 1,4-Addition of Organolithiums to Maleate Monoesters with Application for a Short Efficient Route to Azaindanones

Synlett DOI: 10.1055/s-0040-1707178 The ability of maleate half-ester salts to serve as electrophilic partners in 1,4-conjugate addition reactions with control of regioselectivity has previously been explored in only a limited context with soft nucleophiles. We have demonstrated that benzylic anions of picolines, as well as enolates of ketones, esters, and nitriles, react with lithium 4-(tert-butoxy)-4-oxobutenoate in a completely regioselective manner. This new method was applied to an expedient two-step process for preparing a key azaindanone intermediate for the clinical-candidate drug MK-8666. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - July 13, 2020 Category: Chemistry Authors: Liu, Zhuqing Hyde, Alan M. Klapars, Artis Chung, John Y. L. Lam, Yu-hong Yasuda, Nobuyoshi Tags: cluster Source Type: research