Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220740 | Tetrahedron | 2011 | 5 Pages |
Abstract
Titanium(salalen) complex 1 was an effective catalyst for asymmetric epoxidation of enol esters. Although (E)-enol esters were reluctant to proceed, (Z)-enol esters underwent asymmetric epoxidation to give the epoxides in high yields with high enantioselectivity ranging from 86 to >99% ee in the presence of aqueous hydrogen peroxide as the stoichiometric oxidant. Complete enantioselectivity was observed in the reaction of (Z)-3,3-dimethylbut-1-en-1-yl 4-methoxybenzoate. The obtained epoxide was readily transformed into the corresponding 1,2-diol by reduction with lithium borohydride without erosion of the high enantiomeric excess.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Kazuhiro Matsumoto, Chao Feng, Satoshi Handa, Takuya Oguma, Tsutomu Katsuki,