학술논문
Selective 1,4-Addition of Organolithiums to Maleate Monoesters with Application for a Short Efficient Route to Azaindanones.
Document Type
Article
Author
Source
Subject
*MALEIC acid
*ADDITION reactions
*NUCLEOPHILES
*ENOLATES
*KETONES
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Language
ISSN
0936-5214
Abstract
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. [ABSTRACT FROM AUTHOR]