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Highly enantioselective cyclizations of conjugated trienes with low catalyst loadings: a robust chiral N-heterocyclic carbene enabled by acetic acid cocatalyst
Journal article   Peer reviewed

Highly enantioselective cyclizations of conjugated trienes with low catalyst loadings: a robust chiral N-heterocyclic carbene enabled by acetic acid cocatalyst

Guansai Liu, Phillip D Wilkerson, Christopher A Toth and Hao Xu
Organic letters, Vol.14(3), pp.858-861
02/03/2012
PMID: 22263957

Abstract

Cyclization Heterocyclic Compounds - chemistry Methane - analogs & derivatives Stereoisomerism Methane - chemistry Acetic Acid - chemistry Molecular Structure Catalysis Kinetics
Densely functionalized cyclopentenones are useful synthetic intermediates. We report herein a new method to synthesize this important class of compounds through a highly enantioselective (98 → 99% ee) triene cyclization that is cocatalyzed by acetic acid and a chiral N-heterocyclic carbene (NHC). We discovered that acetic acid not only could coexist with NHCs but also could greatly stabilize the active catalyst, which enables a long-lived catalyst with high reactivity and selectivity.

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