A general method for the synthesis of nonracemic trans-epoxides: concise syntheses of trans-epoxide-containing insect sex pheromones.
A general method for the synthesis of chiral nonracemic trans-epoxides has been developed that provides rapid access to alkyl-, alkenyl-, alkynyl-, and phenyl-substituted trans-epoxides from aldehydes. This methodology has also been applied in concise and high-yielding syntheses of both trans-epoxide containing insect sex pheromones.
Kang
Baldip
B
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, V5A 1S6, Canada.
Britton
Robert
R
D000447:Aldehydes / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C525793:(6Z,9Z,11S,512S)-11,12-epoxyhenicosa-6,9-diene; C525790:(6Z,9Z,4S,5S)-4,5-epoxynonadeca-6,9-diene; D000447:Aldehydes; D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D012724:Sex Attractants