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An Overview on the Robinson Annulation

[ Vol. 22 , Issue. 14 ]

Author(s):

Zai-Qun Liu*   Pages 1347 - 1372 ( 26 )

Abstract:


The Robinson annulation represents a tandem process including the Michael addition and intramolecular Aldol condensation, affording biscyclo[4.4.0]-1-decen-3-one skeleton with cyclohexanone and methyl vinyl ketone (MVK) being substrates. In this review, the Robinson annulation is summarized by subtitles such as catalysis, the finding of equivalent substrates, and some typical applications in the total synthesis, aiming at schematizing achievements of the reaction. The Robinson annulation provides with a model reaction to evaluate the enantioselectivity in the research of organocatalysis. Moreover, attempts to find equivalent substrates instead of cyclohexanone and MVK become targets in the exploration of organic methodology. Finally, the Robinson annulation acts as a strategy widely employed to construct cyclohexenone scaffold in the total synthesis of natural compounds. The aforementioned three facets toward Robinson annulation are still believed to be active topics in the future research on organic reactions.

Keywords:

Robinson annulation, organocatalyst, enantioselectivity, cyclohexanone, methyl vinyl ketone, total synthesis.

Affiliation:

Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021

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