A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of γ-butyrolactones

Catalytic, stereoselective N-heterocyclic carbene-catalyzed reactions facilitate efficient construction of many different heterocyclic compounds, such as the enantioenriched 5-membered (γ) lactones highlighted in this tutorial review. Herein, various strategies to enable formal [3+2] type annulation...

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Bibliographic Details
Published in:Chemical Society reviews 2018-03, Vol.47 (5), p.1773-1782
Main Authors: Murauski, Kathleen J. R, Jaworski, Ashley A, Scheidt, Karl A
Format: Article
Language:English
Subjects:
Butyrolactone
Carbonyls
Catalysis
Chemical reactions
Heterocyclic compounds
Lactones
Nucleophiles
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Summary:Catalytic, stereoselective N-heterocyclic carbene-catalyzed reactions facilitate efficient construction of many different heterocyclic compounds, such as the enantioenriched 5-membered (γ) lactones highlighted in this tutorial review. Herein, various strategies to enable formal [3+2] type annulations between electrophilic carbonyl equivalents and homoenolate nucleophiles for the synthesis of γ-lactones are summarized. Catalytic, stereoselective N-heterocyclic carbene-catalyzed reactions facilitate efficient construction of many different heterocyclic compounds, such as the enantioenriched 5-membered (γ) lactones highlighted in this tutorial review.
ISSN:0306-0012
1460-4744
DOI:10.1039/c7cs00386b