201804-19-5Relevant articles and documents
Chiral ligand-controlled catalytic asymmetric epoxidation of α,β-unsaturated carbonyl compounds with peroxide
Tanaka, Yoshihito,Nishimura, Katsumi,Tomioka, Kiyoshi
, p. 4549 - 4556 (2007/10/03)
Asymmetric epoxidation reaction of α,β-unsaturated carbonyl compounds with alkylperoxide was catalyzed by an external chiral tridentate aminodiether-lithium peroxide giving epoxides with good enantiomeric excess. Slow addition of alkylhydroperoxide was beneficial for a catalytic asymmetric reaction. Lone pair electron-differentiating coordination of a carbonyl oxygen to lithium is another critical factor for high enantioselectivity.
Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain
Adger, Brian M.,Barkley, James V.,Bergeron, Sophie,Cappi, Michael W.,Flowerdew, Benjamin E.,Jackson, Mark P.,McCague, Ray,Nugent, Thomas C.,Roberts, Stanley M.
, p. 3501 - 3507 (2007/10/03)
Poly-L-leucine catalyses the asymmetric epoxidation of enones 1-6 efficiently in a non-aqueous medium to provide the epoxy ketones 7-12 (70-91% yield; 80 to ≥95% ee). The strategy was used to make diltiazem 16 and the Taxol side chain 23 in single enantiomer form.
