Comparative enantiocontrol with allyl phenyldiazoacetates in asymmetric catalytic intramolecular cyclopropanation.
Dirhodium(II) azetidinone-carboxylates are effective asymmetric catalysts for diazo decomposition of allyl diazoacetates and their subsequent intramolecular cyclopropanations. The effect of alkene substituents on enantiocontrol has been examined and modest selectivities have been achieved. Steric influences from substituents on the diazo carbon are seen to diminish enantioselectivities.
Doyle
Michael P
MP
Department of Chemistry, University of Arizona, Tucson 85721, USA. mdoyle@u.arizona.edu
Hu
Wenhao
W
Weathers
Thomas M
TM
D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003521:Cyclopropanes; D003979:Diazonium Compounds; C035176:benzenediazonium; C030797:cyclopropane