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DOI: 10.1055/sos-SD-201-00050

Colonna, S.; Perdicchia, D.Science of Synthesis: Stereoselective Synthesis, (20111125.

The α-poly(amino acid)-catalyzed JuliàColonna 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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Meee(eeeee eeee) Meeeeeee (MM)e Meee (e) Meeee (%) ee (%) Mee
e-Mee (8888) 88 88 88 [‌88‌]
e-Mee (8888) 88 88 88 [‌88‌]
e,e-Mee (8888) 88 8 8 [‌88‌]
e-Mee (8888) 88 88 88 [‌88‌]
e-Mee (8888) 888 8 88 [‌88‌]
e-Mee (8888) 888 8 88 [‌88‌]
e-Mee (8888) 88 88 88 [‌88‌]
e-Mee (8888) 88 88 88 [‌88‌]
e-Meeeee (8888) 88 88 88 [‌88‌]
e-Mee (8888) 88 88 8 [‌88‌]
e-β-Me-Mee 888 8 8 [‌88‌]
e-β-Me-Mee 888 88 88 [‌88‌]
(e-Mee-e-Mee)88 88 88 88 [‌88‌]
(e-Mee-e-Mee)88 88 88 88 [‌88‌]
e-Mee-e-Mee 888 88 8 [‌88‌]

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

Meeeeeeeeee 8

M8 M8 Meee (e) Meeeeee Meeee (%) ee (%) Mee
Me 8-eeeeeee 88 eeeeeee 88 88 [‌88‌]
Me 8-eeeeeee 88 eeeeeee 88 88 [‌88‌]
Me 8-eeeeeeee 88 MMe8 88 88 [‌88‌]
8-eeeeeee Me 88 MM8Me8 88 88 [‌88‌]
8-eeeeeee 8-eeeeeeee 88 MM8Me8 88 88 [‌88‌]
8-eeeee 8-eeeeeeee 88 MM8Me8 88 88 [‌88‌]
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eeeeeeeeeee 8-eeeeeeee 88 MM8Me8 88 88 [‌88‌]
e-Me e-Me 88 eeeeeee eeeee 88 [‌88‌]
Me Me-Me 88 eeeeeee 88 88 [‌88‌]

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

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