2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides.
[reaction: see text] Reaction of hindered lithium amides with readily available (enantiopure) terminal epoxides gives 2-ene-1,4-diols via carbenoid dimerization of the corresponding alpha-lithiated epoxides. D-Mannitol and D-iditol were synthesized using this method in three steps from (S)-tritylglycidyl ether.
Hodgson
David M
DM
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Bray
Christopher D
CD
Kindon
Nicholas D
ND
D000438:Alcohols / Q000138:chemical synthesis*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D005995:Glyceryl Ethers / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008353:Mannitol / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D000438:Alcohols; D000577:Amides; D004852:Epoxy Compounds; D005995:Glyceryl Ethers; D013402:Sugar Alcohols; D008353:Mannitol; C082913:iditol; D008094:Lithium