Science of Synthesis

Colonna, S.; Perdicchia, D., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 125.

The α-poly(amino acid)-catalyzed Julià–Colonna epoxidation has emerged as an efficient method for the enantioselective functionalization of α,β-unsaturated ketones. Since its discovery in 1980, the reaction conditions have been continually optimized. The original procedure for epoxidation of electron-deficient alkenes was based on a triphasic system comprising a poly(amino acid), an aqueous phase, and an organic phase.[‌10‌,‌11‌]

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‌Meeeee 8‌ Meeeeeeeeee ee (M)-8,8-Meeeeeeeeeee-8-ee-8-eee eeee Meeeeee Meee(eeeee eeeee)[‌88‌]

‌Meeeeeeeeee 8‌

e MM = eeeeeee eeeeeeeee eeeeee.

Mee eeee eeeeeeeeeeeeeeeeeeee eee eeeeeeee eeee eeee(e-eeeeeee) ee eeee(e-eeeeeee), eee ee eeee eeeeeeeee eeee eeeeeee eee eeee eeeeeeee eeee eeee(e-eeeeeeeeee). Me eeee(e-eeeeeee) ee eeeeee ee eee eeeeeeee eeee(eeeee eeee), 8,8-eeeeeeeeee-8-ee-8-eee eeeeeeeeeee ‌88‌ eeee eeeeeeeeeeee eeeeeee eeeee eeeeeeee eeeeeeeeee (‌Meeeee 8‌).[‌88‌] Me eeeeeeee, e-eeeee eeeee eeee eeeeeeee eeee eee eeeeeeee eeeeeeee eeeeeeeeeeeeeee.

‌Meeeee 8‌ Meee(e-eeeeeee)-Meeeeeeee Meeeeeeeeeee ee Meee-8-ee-8-eee Meeeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

Mee eee ee eeeeee eeeeeeee ee eeeeeeeeee eeeee eeeeeeee eeee eeeeeee eeeeeeeee eeeeeee ee eeeeeeeee.[‌88‌] Meeeee eeeeeeee eee M- eee M-eeeeeeee eeeee ee eee eeeeeeeeeee, eeeeeee, eee eeeeee eeeeee ee eee eeeeeeee ee eee eeeeeeee.[‌88‌]

Meeeeeeee eee eeeeeee eeeee ee e eeeeee eeeee eeeeeee eeeee eeeeee ee ee ee eeeeeeeeee eeeeeeee, eee eeee eee ee eeeeeeee eeeeeee eee eeeeeeee ee e eeeeeee-eeeeee eeeeeeeeeee eeee eeee(eeeeeee)-M-eeeeeeeeeeeeeeee ee eeee e eeeeeee eeee eeeeeeee eeeeee ee eeee ee eee eeeeeeee eeeeeee ee eee eeeeeeee.[‌88‌] Me eeeeeeeee eeeeee-eeeeeee eeee(e-eeeeeee) eeeeeeee eee eee eeeeeeeeee eeeeeeeeeee ee (M)-8,8-eeeeeeeeeeee-8-ee-8-eee (eeeeeeeeeeeeeeeeee)[‌88‌] eeeee eee eeeeeeeeeeeee eeeeeee eeee eeee eeeeeeeeeeeeeeeeee ee ee ee 88% ee. Mee eeeeeeee eee ee eeeeee eeeeeeeee eeee eee eeeeeeee eeeeeee eee eeeeee eeeeeee eeeee eeee ee eeeeeeeeeee eeee ee eeeeeeee.

Mee Meeeà–Meeeeee eeeeeeee eee ee eeee ee eeeeeee eee eeeeeeeee ‌88‌ ee e eeeeeeeeeee eeeeeeeeee ‌88‌ eeee eee 8,8-eeeeeeeeee-8-ee-8-eee eeeeeeeeee ‌88‌; eeee eeeeeeee eee ee eeeeee ee ee eeeeeeeeee ee eeeeeee eeeeeee eeeee (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeeee ee e Meeeeeeee ee e Meeeeeeeeee Meeeeeeeee[‌88‌]

Mee eeeee-eeeee eeeeeeee eeeeeeeeee eee eeee ee eeee ee eeeeeeeee eeeeeeeee, eeeeee, eee eeeeeeee (‌Meeeee 8‌).[‌88‌,‌88‌] M eeeeeee eeeeee ee eeeee eeeeee eee ee eeeeeeeeeeee ee eee eeeeeeee eeeeee eeee ee ee eee eeeeeeee β ee ee.

‌Meeeee 8‌ Meeeeeeeee Meeeeeeee ee α,β-Meeeeeeeeee Meeeeee[‌88‌,‌88‌]

Mee eeeeeeeeeee ee eee eeeee-eeeee Meeeà–Meeeeee eeeeeeee eee eeee eee eeeeeee eeeeeeee ee eee eeeeeeeeeeee eeeeeeeee ee eeeee eeeeeeeeee, eee eeeeeeeeeeeeee eeeeeee ee ee eeeeeee ee eeeeee eeee eee eeeee eeeeeeeee ee 8,8-eeeeeeeeee-8-ee-8-eeee, eee eee eeeeeeee eeeee e eee ee eee eeeeeeee eeeeeee, eeeeeee eeee eeeeeeeeee eee eeeeeeeee eee eeeeeeee eeeee eee eeeeeeeeee ee eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

8-Meeeeeee{(8M,8M)-8-[8-(8-eeeeeeeeeee)eeeeee]eeeeee-8-ee}eeeeeeeee (‌88‌):[‌88‌]

MMMMMMM: Me ee eeeeeeee eeeeeeeeeee eeee eeeeee eeeeeeee eeeeee ee eeeeeeeee ee eee eee ee eee eeeeeeee eeeeee eeeeeee eeeeee.

M eeeeeee eeee ee MeMM (888 e, 8.888 eee) ee M8M (888 eM) eee eeeeeee eeeeeeeeeeee eeee eeee(e-eeeeeee) [eeeeeeeee eeeeee 8888–88 888 (Meeee Meeeeeee Me.), 888 e], eeeeee (88% eeeeee, 8.8 M), eee eeeee ‌88‌ (888 e, 8.888 eee). Mee eeeeeeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 e eee eeee eeeeee ee 88–88 °M. Meee, eeee (8.8 e) eee eeeee, eeeeeeee ee 88% ee M8M8 (8.888 M, 88.88 eee) eeeee eeeeee (8 e) eeeee eee eeeeeee ee eee eeeeeee eeee e eeeeeeeeeeeee eeee eeeeeeee ee e eeeeeeee eeeeee ee eeee e eeee eeee eee eeeeeeee eeeeeeeeeee eee eee eeeeee 88 °M. Mee eeeeeee eee eeee eeeeeee eee 88 e ee ee eeeeee e eeee ee MeMM (8.8 e, 8.888 eee) ee 88% ee M8M8 (888 eM, 8.88 eee) eee eeeee eee eee eeeeeee eee eeeeeee ee 88–88 °M eee ee eeeeeeeeee 8 e. Mee eeeeeee eee eeee eeeeeee eeee MeMMe (888 eM) eee eeeeeeee. Mee eeeeee eeee eeeeeeeeee ee eeee(e-eeeeeee) eee eeee eeeeeee eee eeeeee eeee MeMMe (888 eM) eee eeee eeeeeeee ee eee (88–88 °M) MeMMe (8.8 M) eee 88 eee eee eeeeeeee eeeee. Mee eeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeee eeee M8M (8 × 888 eM) eee eeeee (8 M), eee eeee eeeee [MeMM8 (888 e)], eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee e eeeee eeeee eeee eee eeeeeeeeeeee [eeeeee/eeeeeee 88:8 (8.8 M)]; eeeee: 888 e (88%); 88% ee.

References