Asymmetric epoxidation catalyzed by alpha,alpha-dimethylmorpholinone ketone. Methyl group effect on spiro and planar transition states.
Asymmetric epoxidation of olefins by using an alpha,alpha-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The alpha,alpha-dimethyl group has significant impact on spiro and planar transition states.
Wong
O Andrea
OA
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Wang
Bin
B
Zhao
Mei-Xin
MX
Shi
Yian
Y
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009025:Morpholines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*
D000475:Alkenes; D004852:Epoxy Compounds; D007659:Ketones; D009025:Morpholines; D013141:Spiro Compounds