Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups

The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to...

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Published inOrganic & biomolecular chemistry Vol. 9; no. 22; pp. 7849 - 7859
Main Authors Tello-Aburto, Rodolfo, Kalstabakken, Kyle A., Volp, Kelly A., Harned, Andrew M.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 26.10.2011
Subjects
Catalysis
Chemistry
Chemistry, Organic
Chemistry, Pharmaceutical - methods
Cinchona - chemistry
Cinchona Alkaloids - chemistry
Cyclization
Cyclohexenes - analysis
Cyclohexenes - chemistry
Cyclopropanes - analysis
Cyclopropanes - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
ASYMMETRIC PHASE-TRANSFER
QUINOLS
REAGENTS
HYPERVALENT IODINE OXIDATION
PHENOLS
DESYMMETRISATION
SPIROLACTONIZATION
DEAROMATIZATION
DESYMMETRIZATION
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Summary:The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob06125a