JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
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Enantioselective (4+2) Annulation of Donor-Acceptor Cyclobutanes by N-Heterocyclic Carbene Catalysis.

Angewandte Chemie 2016 December 24
Herein we report the enantioselective (4+2) annulation of donor-acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.

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