Stereoselective Multicomponent Reactions Using Zincate Nucleophiles: β-Dicarbonyl Synthesis and Functionalization.
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.
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
Stephen K
SK
Murphy
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
Mingshuo
M
Zeng
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.|Department of Pharmacology, Yale School of Medicine , New Haven, Connecticut 06520, United States.
Seth B
SB
Herzon
D000215:Acylation; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D061565:Cycloaddition Reaction; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D007659:Ketones; D009942:Organometallic Compounds; C520093:methyllithium; D015032:Zinc
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