Article

Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups.

Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
Organic & Biomolecular Chemistry (impact factor: 3.7). 09/2011; 9(22):7849-59. DOI:10.1039/c1ob06125a
Source: PubMed

ABSTRACT 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.

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Keywords

2,5-cyclohexadienones tethered
 
activated methylene groups
 
Cinchona alkaloid-based phase-transfer catalyst
 
cyclohexadienone ring
 
prochiral cyclohexadienones
 
regioselectively direct
 
substitution
 

Rodolfo Tello-Aburto