The development of a facile tandem Wolff/Cope rearrangement for the synthesis of fused carbocyclic skeletons.
A set of mild processes for the conversion of vinyl cyclopropyl diazo ketones to highly functionalized cycloheptadienones and vinyl cyclopentenones by use of a target-inspired tandem Wolff/Cope rearrangement sequence is described. A divergent reaction course of the vinyl cyclopropyl diazo ketone substrates under sono- or photochemical activation provides good to excellent yields (55-98%) of the product cycloheptadienones and vinyl cyclopentenones.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Richmond
R
Sarpong
Julius T
JT
Su
Brian M
BM
Stoltz
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003508:Cycloheptanes / Q000138:chemical synthesis*; D003516:Cycloparaffins / Q000138:chemical synthesis*
D001643:Bridged Bicyclo Compounds; D003508:Cycloheptanes; D003516:Cycloparaffins; C000363:cycloheptanone