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

ABSTRACT: A general strategy for conjugate addition-C-acylation that enables the synthesis of enantioenriched ?-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.

SUBMITTER: Murphy SK

PROVIDER: S-EPMC7000105 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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

Murphy Stephen K SK Zeng Mingshuo M Herzon Seth B SB

Organic letters 20160927 19

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 tran ...[more]

PMID: 27670226

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