Stereoselective Multicomponent Reactions Using Zincate Nucleophiles: β-Dicarbonyl Synthesis and Functionalization

• DOI: 10.1021/acs.orglett.6b02320
• Publication Date: 2016-09-27T12:07:38Z
• Authors: Stephen K. Murphy; Mingshuo Zeng; Seth B. Herzon
• Keywords: Zinc; Cycloaddition Reaction; Molecular Structure; Acylation; Organometallic Compounds; Stereoisomerism; Chemistry Techniques, Synthetic; Ketones; 01 natural sciences; Catalysis; 0104 chemical sciences

A general strategy for conjugate addition-C-acylation that enables the synthesis of enantioenriched β-dicarbonyl compounds is described. A novel method for derivatizing these adducts by stereo- and site-selective zinc-catalyzed addition of alkyllithium reagents is also reported. These reactions can be performed in tandem to achieve an enantio- and diastereoselective four-component coupling. The in situ generation of weakly basic lithium zincate species is central to the success of all three transformations.