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Org Lett. 2016 Oct 7;18(19):4880-4883. Epub 2016 Sep 27.

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

Author information

1
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
2
Department of Pharmacology, Yale School of Medicine , New Haven, Connecticut 06520, United States.

Abstract

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.

PMID:
27670226
DOI:
10.1021/acs.orglett.6b02320
[Indexed for MEDLINE]

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