Deprotonation-electrophile trapping of terminal epoxides.
Organolithium-induced deprotonation of terminal epoxides in the presence of appropriate diamine ligands allows trapping with a range of electrophiles, yielding functionalised di- and tri-substituted epoxides in good yields and with control of stereochemistry at the epoxide.
Hodgson
David M
DM
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UKOX1 3TA.
Kirton
Eirene H M
EH
Miles
Steven M
SM
Norsikian
Stéphanie L M
SL
Reynolds
Nigel J
NJ
Coote
Steven J
SJ
D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011522:Protons; D013055:Spectrophotometry, Infrared
D004852:Epoxy Compounds; D011522:Protons