Traceless chiral auxiliaries for the allene ether Nazarov cyclization.
The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.
Banaag
April R
AR
University of Hawaii, Chemistry Department, Honolulu, Hawaii 96822, USA.
Tius
Marcus A
MA
D000466:Alkadienes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D004986:Ether / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D003517:Cyclopentanes; D004986:Ether; C007201:cyclopentanone; C025947:propadiene