Accessible sugars as asymmetric olefin epoxidation organocatalysts: glucosaminide ketones in the synthesis of terminal epoxides.
A systematically varied series of conformationally restricted ketones, readily prepared from N-acetyl-D-glucosamine, were tested against representative olefins as asymmetric epoxidation catalysts showing useful selectivities against terminal olefins and, in particular, typically difficult 2,2-disubstituted terminal olefins.
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, UK OX1 3TA.
Omar
O
Boutureira
Joanna F
JF
McGouran
Robert L
RL
Stafford
Daniel P G
DP
Emmerson
Benjamin G
BG
Davis
D000475:Alkenes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D002241:Carbohydrates; D004852:Epoxy Compounds; D007659:Ketones