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Please login or sign up for a free trial to access the full content.1.1.1.2 Sharpless Asymmetric Dihydroxylation of Alkenes
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Muñiz, K., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 10.
This variant of the osmium-promoted reaction permits an enantioselective 1,2-dihydroxylation of alkenes.[1,20–22] The reaction has a broad substrate scope and a characteristic selectivity, and it represents one of the most reliable asymmetric homogeneous catalytic processes developed to date.
Mee eee eeeeeee ee eeee eeeeeeee ee eeeee ee ee eeeeeeee eeeeeeeeeee ee Meeeeee, eee eeeee eeee eee eeeeeeee ee eeeeeeee eeeeeeeeeeeee eeeeeeee eee eeeeeee eeee ee eeeeeeeeeeeeeee.[88] Mee eeeeeeeee ee e eeeeeeeeeeee eeeeeee ee eeeeee(MMMM) eeeee[88,88] eeeeeeee Meeeeeeee ee eeeeeee eeeeee eeeeeeee eeeeeeee eeeeeeeeeee ee eeeeeee ee eee 8,8-eeeeeeeeeeeeeee ee eeeeeee. Meee eeeeeeeeeee eeeeee eeeeeee ee eeeeee ee e eeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeee. Mee eeeeeeee eeeeeee eee eeeeeee ee eeeeee-eeeeeeeeeee eeeeeeeee.[88] Meeee, eee eeeeeee eeeeee(MMMM) eeeee eeeeeeee eeeeeeee e eeeeeeeeeeeee eeeeeeee eeeeeeee eeee ee eeeeeeeeee eeee eee eeee eeeeee(MMMM) eeeee. Meee eeeeeee eeeeeee eeeeeeeee eeeeeee ee eeeee ee eee eeeeeeeeeeeeeeee eeeeeee.
Mee eeee eeeeeee eeeeeeee ee eeeeeeeee eeee eeeeeee eeee eeeeee eeee eee eeeeeeee eeeeeeee eeeeeeee eeeeeeee ee e eeeeeeeeeee eeee. Meeee eeeeeee eeeeeee eeeeee eeeeeeeeeeeeee [ee eee eeee ee (MMM)8MMMM] ee eeeeeeeeeeeeeeee [ee eee eeee ee (MMMM)8MMMM] ee eeeeee eeeee (Meeeee 8).
Meeeee 8 Meeeeeee Meeeeeee–Meeeeeeeeee Meeeeee eee Meeeeeeeeeeeeeee Meeeeeeeeeeeeee
Meeeeeee eee eee eeeeee eeeeeeee eeeee eee eee eeeeeeeeeee, eee eeeeeeeeeeeee ee eeee eeeee, eeeee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeeee eee eeeee eeee eeeeee ee eeeeeeeeeeeeeeeee. Mee eeee eeeeeeeeeee eee eeeeeee ee eeeeeeeee eeeeeeeee eee eeeee eeeeeeee ee Meeeee 8. Meee, MM eeeeeee eee eeeeeee eeeeeeeeeee, eeeeeeeeeeeeee e eeee eeeeeeee eeeeee ee e eeeee eeeeeeeee eeeee. Meeee eeeeeeeeeeee eee eeeeee eeeeeeeeeee, eeee MM eeeeeeeee ee eeeee eeeeeeeeeeee eee MM ee eeeeee-eeeee eeee. Meeeee eee eeeeeeeeee eeeee, eee eeeeee eeeeeeeeeee ee eeeeeeee ee ee eeee eee eeeeee eeeeeeeee ee eee eeeeee eee eeeeee ee e eeeeeeee eeee ee e eeee eeeee eeeeeeeeeee.
Meeeee 8 Meee eee Meee Meeeeeeeeee ee Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeee (Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeee Meeeeee)[8,88]
Meeeeee eeee eee eeeeeeeeee ee eee eeeeee eeeeee/eeeeee eeeeeee ee eeeeeeeeee eeee eeeee eeeeeeeeeee eeee ee eeeeeeee eeee eee eee eeee (e.e., eee B-eeee) ee eee eeee ee eee (MMMM)8MMMM eeeeee, ee eeee eee eeeeee eeee (e.e., eee a-eeee) ee eee eeee ee eee eeeeeeeeeeeee (MMM)8MMMM eeeeee.
Meeeeeee eee eeeeeeee eee ee eeeeeeeee eeeee eeeeeee eeeeeeeeee, e eeeeeeeeeee ee eeeeeeeee eeeeee(MM) {M8[MeM8(MM)8]} ee eeeeeeeeeee eeeeee eeeeee, eeeeeeeee eeeeeeeeeeeeeeee(MMM) ee eeeeeeeee, eee eeeeeeeee eeeeeeeee ee eeee eeeeee e eeeeeee eeeeeee ee eeee-eeeee eeeeeee eee eeeee (8:8 e/e) ee eeeeeee eee eeeeeeeee eeeeee. Me eeee eeeee, eeeeeeee ee eeeeeeeeeeeeeeeeee eee eeee ee eeeeeeeeee eeeeeeeeee eeeeee ee eee eeeeeeee eeee.
Mee eeeeeeee eeeeeeee eeeee eee e eee-eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeee eee eee eeeeeeee eeeeeeeeee. Mee eeeeeeeee eeeeeeee eee eeeeeee eeeee ee MM-eee-a [eeeee ee (MMM)8MMMM] eee MM-eee-B [eeeee ee (MMMM)8MMMM], eeeeeeeee ee eee eeeeeeeeeeee eeee eeeeeeeeeee ee eee eeeeee eeeeeeeee ee eee eeeeeee.[88]
Mee eeeee ee eee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eee eeeeeee eeeee ee Meeeee 8. Me eeeeeeeee eeee eee eeeeeeee eeeeeeeee eeeeeeee, (M)-8,8-eeeeeeeeeeeeee [(M)-eeeeeeee] eeeeeeeeee ee eeeeeee eeeeeeeee eee eee eeeeeeeeeeeeeeee eeeeeeeeeeeeeee eee, eee eeee eeeeeee, eeeee eeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeee eeee eeeeeee eeee 88.8% eeeeeeeeeeee eeeeee. Mee eee eeeeeeee eeee eeeee eee (MMMM)8MMMM eeeeee, ee eeeeeeeee, eee eeeeeeee eeeeee eeee eee B-eeee eeeeeee ee eee M,M eeeeeeeeeeeee.
Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee (M)-8,8-Meeeeeeeeeeeee[88]
Mee eeeeeee eeeeeeeee eeeee eee eee eeeeee-eeeeeeeee eeeeeeeeeeeeeee ee eeeeeee ee eeeeee eeeeeee. Meeee eee eee eeeeeeeee eeeeee, eeeee eee eeeeeeee ee ee “eeeee eeeee” eee “eeeeeeeee eeeee” (Meeeee 8). Mee eeeeee ee eeeeeeeeeee eee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee. Me eeeeee ee eeeeeeeeee eeeeeeeeeeee eeeeeee eeeeee(MMMM) eeeee eee eee eeeeee eeeeee. Meeeee-eeeeeeeeeee eeeeeeee ee eeee eeeeeee ee eee eeeeeeeee eeeeee eeeee ee eeeeee(MM) eeeeeeeee, eeeee ee eeeeeeee ee eee eeeeeeeeeeeee eeeeee(MMMM) eeeeeeeee. Meeeee-eeeeeeee eeeeeeeeee ee eeee eeeee eeeeeeeeeee eeeeee(MMMM) eeeee eee eeeeeeee eee eeee eeee. Meeeeeee eeee eeee eeeeeee eeeeeee eeee eeeeeeeeeeee eeeeeeee eee ee eee eeeeeeeee eeee eeeeeeeeeee ee eee eeeeeeeee eeee. Mee eeeee eeeeee ee eeee eeee ee eee eeeee eeeeeeeeee. Meeeeee eeeeeeeeeee eeee[88] eee eeeeeeeeeee eeeeeeeeeeee[88] eeeeeee e eeeeeeeee [8 + 8] eeeeeeeeeeeee[88–88] ee eeeeeeeee eeee e eeeeeeee eeeeeeeee.[88–88] Meeeeee eeee-eeeeeeeeeee eeeeee ee eeeeeee eee eee eeeeeeeeeeeeeee eeee eeee eeee eeeeeeeee.[88–88]
Mee eeeee eeeee ee eeeee eee eeeeee-eeeeeeee eeeeeeeeee eeee eee eeeeeee eeeeeee, eee eeeeeeeeeeee eeeeee(MMMM) eeeeeeeee eee eeeeee eeeeeee ee eeeeee eeeeeee ee eeeeee(MM) eee(eeeeeeeee). Mee ee eee eeee eeee eeee eeee eeeeeeee eeee eeee eee eeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee, eee eeeeeeee eeeeeeee eeee eee eeeeeeeeeeeeeeeeee. Me e eeeeeeeeeee, eeeeeeeeee eeeeeeee e eeee eeeeeee eeee eeee eee eeeeeeeeeeee eeeeee. Mee eeeeeeeee eeeeeeeeeeeee eeeeeee, eeee eeeee eeeeeeeeee, eeeeee eee eeeeeeeee eeeeeeeee eeeee. Meeee eeeeeeeeeee eeeeeee eee eee eeeeee eeeeeeeee eeeeeeeeeee e eeeeeee ee eee eeeee eeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeee, eee eeeeeeeee eeeeeeeeee, eeeeeeeeee eee eee ee eeeeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeeeeeeeee(MMM) ee eeeeeeeee, eeeeee eeeeeeee eeeeeeee eeeeee eee eeeee eeeee.
Meeeee 8 Meeeeeeee Meeeee eee eee Meeeee(MMMM)-Meeeeeeee Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeee[8]
Me eeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eeeee eeeeeeeee eeee eee e eeeee eeeeee ee eeeeeee. Meeee 8 eeeee eee eee eeeeeee ee eeeeee eeeeeeeee eee eeeeeee eee eeeeeeeee eeeeee eeeee.
Meeee 8 Meeeee Meeeeee eee Meeeee Meeeeeeeeee[8]
Meee eee ee eee eee eeeeeee eee eeeeeeeee ee eeeeeeeeeeee eeeeeeee eeeee eee eeeeeeeeeee (MMMM) eeeeee eeeee. 8,8-Meeeeeeeeeeee, M-8,8-eeeeeeeeeeeee, eee eeeeeeeeeeeeee eeeeeee eee eeeeeee eeeeeeee eeee eeeee eee eeeeeeee eeeeeeeeeee (MMMM) eeeeeee, eeee eeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeee 88 eee 88.8%. Meeee eeeeeee eeee eeee eeee eee eeeeeeeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeee, eeeeeeee eeee eee ee eeeeeeee ee eeeeeee eeee e eeeeeeeeee eeeeee (MMM).[88] Me ee 88% ee eee ee eeeeeee eee eeeee eeeeeeeeee. Meeeeeeee, eee eeee eeeeeeeeeee eeeeeee eee eeeee eeee e M-8,8-eeeeeeeeeeeeee eeeeeee. Meeee eeeeeee e eeeeeee eeeeeeeee-eeeeeeeeeeeeee eeeeeeee (MMM)[88] eee eeee eeeeeeeeeeee eeeeee eeeeee ee eee eeeee ee 88–88%. Meeeeee 8–88 eeee eeeeeeee eee eee eeeeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee ee eeeee eeeeee eeeeeee.
Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeee Meeeeee[8,88,88,88–88]
Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee 8,8′-Meeeeeeeeeeee Meeeeee[8,88,88,88,88]
Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee M-8,8-Meeeeeeeeeeee Meeeeee[8,88,88,88–88]
e Meeeeeee ee eeee eeeeeeeeeee.
e MM-eee-a eee eeee.
e 8 Meeee ee MeMMM8 eee eeeee.
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeee[8,88]
e 8 Meeee ee MeMMM8 eee eeeee.
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeeeee Meeeeee[88]
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee M-8,8-Meeeeeeeeeeee Meeeeee[88,88]
e Meeeee eeeeeee eee 8 eee% eee (MMMM)MMM eee 8 eee% eee (MMM)8MMM.
Mee eeee eeeeeee eeeeee eeeeeee, eeee ee eeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeee eeee eee eee ee ee eeeeeeeeeee eeeeee eeeeeee ee eeeeeeeeeeeee eeeeee (MMM eeeeeee) (Meeeee 88).[88]
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeee Meeeeee eeee e Meeeee Meeeee Meeeeeeeee ee Meeeeeeeeeeee Meeeee[88]
e Meeeee: 88–88%; eeeeeeeeee eeeeee eee eeeeeeee.
Meeeeee eeeeeee ee eeeeeeeeeeeee eeeeee (MMM-eeee eeeeeee) eeee eeee eeee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeee ee e eeeeee ee eeeeeeee eeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeeeeeee Meeeeeee eee Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeee Meeee e Meeeee Meeeee Meeeeeeeee ee Meeeeeeeeeeee Meeeee[88]
e Meeeee: 88–88%; eeeeeeeeee eeeeee eee eeeeeeee.
Meeeeee eeeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeeeeee ee eeee eeeeee. Meeee eeeeeeeee eeeeeee eeeeeeeeeeeeeee eeeeee ee 8-eeeeeee eeeeeeee eeeeeeeee. Meeee, eee MMMM eee MMM eeeeeee eeeeeeeee eee eeeeeee ee eeeeee (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee Meee Meeeee[88,88]
e Meeeee eee eeeeeeee.
e Meeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eeeeeee.
Mee eeeee ee eee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeee eee eeee eeeeeee eeeeeeeeeeee eee eee eeeeeeeeeeeeeeee ee eeeeeeee, eeee ee eeeeeeee (Meeeee 88). Meee e eeeeeeeeeeeeee eeeeeeeeee e eeeee eeeeeeeee ee eeee eeeeeeeeeee eeeee ee ee eeeeeeeeee ee e eeeeeee eeeeee ee eeeee ee eeeeee ee e eeeeeee eeee eeee eeeeeeeeeeeeee eee eeeeeeeeeeee eeeeee. Meeeee, eeeee eee eeeeeeee eeeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeee ee eeeeeee ee eeeeeeeeee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeee eeee eeeeeee ee 88% eeeee. Me eeeeeee, eeee eeeeeeee eeeeeeeeeeeeee eeeee eeeeee eeee ee eeeee 88% eeeeeeeeee eeeeeeeee eee 88% eeeee eee eeeeeeeeeeeeeee eeee.[88]
Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeeee ee Meeeeeee Meeee eee Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeee[88]
Me e eeeeeeeee eeeeeeeeeee, eeeeeeeee eeee-eeeeeeeeeeeeeee ee eeeeeeee eeeeeeeeee e eeeeeeeee eeeeeeee eeeeee eee eeeeeeeeeeeeeee ee eeeeeeeeee eeeeee eeeee eee eeee eeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee eeeee. Mee eeeeeeeeeeeeeeee ee eeee eeeee ee eeeeeeeeee ee eeeeeeeeee ee eeee ee eeeeee eeeeeee. Mee eeeeeeee eeeeeee, eee eeeee ee eee eeeeeeeeee eeeeeeeeeeeeeee eee eeeeeeeeeeeee eeeeee eee M-8,8-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeee eee M-8,8-eeeeeeeeeeeee eee eeeeeeee eeeeeee.[88] Meeeeee eeeeee eee eeeeeeee ee eeeeeee eeeeeeeee eeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeee. Meeee 8 eeeee eeeeeeee ee eeee eeee ee eeeeeeeeeeeeee. Me eeee ee eeeeeeeee ee eeeeeeee eeeeeeee, eee eeeee eeeeeeeeeee ee eeeee.
Meeee 8 Meeeeeeeee Meee-eeeeeeeeeeeeeee ee Meeeeeeeeeeee Meeeee[8,88–88]
e e.e. = eee eeeeeeee.
e 88% ee.
e 88:8 eeeeeeeeeeeeeeee.
e 8:8 eeeeeeeeeeeeeeee.
e >88:8 eeeeeeeeeeeeeeee.
e 88:8 eeeeeeeeeeeeeeee.
Meeeeeee eeeeee ee eeeeeee eeeeeeee eee ee eeeeeeee eeee eee eeeeeeeeeeeeeee ee eeee-8,8-eeeeee. Meeeeeee eee eeeeee ee eeeeeeee eeeeeee ee eeeeeeeee e eeeeee eeeeeeeee eeeee eee eeeeeeee eeeeee eeeee eeeeeeeeeeeeeee ee eeeeeee ee eeee ee eeee eeee eeeee eee eeeeeeeee eeeeeeeeeeee eeeeeeee (Meeee 8).
Meeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeee Meee-8,8-eeeeee eee Meee-8,8,8-eeeeeee[88,88]
e Meeeeeee eeeee.
Meeeeeee eeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeeeee ee eeeeee. Mee ee eee eeeeeeeeee ee eeeeee(MMMM) eeeee eee eeeeee eeeeeeeee, eeeeeeeee eeeeeeeee ee eeeee ee eeeeeeee eeee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee eeeeee. Meeeeeeeeeee eeeeee eeeeee eee ee eee eeeee 88–88% eee eeee eeeeee (88–88%) eee eeeeeeee.[88]
Me eeeeeeeeeee ee Meeeeeee[88,88] eee Meeeeeeee[88] ee eeeeeeeeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee eeee eee Meñee ee eeeeeee ee eeeeeeeeeeeeeeee eeeeeee ee eeee eeeeeeee. Meeee, ee eee eeeeeeee ee ee eeeeeeeeeee eeee eeeee eeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeee eeeee MMMM eeeeeee, eeeeeee eeeeeeee eee eeeeeeee eeeeeee 8 eee ee eeeeeeeeeee eeeeeeee eeee eeeee eeeeeeeeeeeee eeeeee eeeeeee eeeeee 8 (Meeeee 88).[88] Mee eeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeee eeeeeee eeee eeee eee eeeeeeeeeeeee eeee eeee eee eeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeee.
Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeeee ee Meeeeee eeee Meeeee Meeeeee Meeeee eeeee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
MM-eee:[88]
MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.
M8[MeM8(MM)8] (8.88 e, 8.88 eeee) eee (MMM)8MMMM (eee MM-eee-a; 8.88 e, 8.88 eeee) ee (MMMM)8MMMM (eee MM-eee-B; 8.88 e, 8.88 eeee) eeee eeeeee eeeeeeee ee eeee e eeee eeeeee, eeee eeeee ee eeeeeeee M8[Me(MM)8] (888.8 e, 8.88 eee) eee eeeeeeee M8MM8 (888.8 e, 8.88 eee), eee eeeeeee eeeee ee e eeeeeee ee e eeeeee eee eeeee 88 eee. Mee eeeeeeeee eeeeeee eeeeee ee eeee eee eee ee eeeee eee eee.
(M,M)-8,8-Meeeeeeeeeeeee-8,8-eeee (8, M8 = M8 = Me); Meeeeee Meeeeeeee Meeee MM-eee-B:[88]
MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.
M 88-eM, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eeeeeee eeee e-MeMM (8 eM), M8M (8 eM), eee MM-eee-B (8.8 e). Meeeeeee ee eeee eeeeeeeeeee eeeeeeee eee eeeee eeeeee; eee eeeee eeeeeee eeeee eee eeeeee eeeeee. MeMM8 (88 ee, 8 eeee) eee eeeee ee eeee eeeee. Mee eeeeeee eee eeeeee ee 8 °M, eeeeeeeee eeee ee eee eeeeeeeee eeeee eeeeeeeeeeee. (M)-8,8-Meeeeeeeeeeeee (8 eeee) eee eeeee ee eeee, eee eee eeeeeeeeeeeee eeeeee eee eeeeeee eeeeeeeeee ee 8 °M eee 88 e. Meeee eee eeeeeee eee eeeeeee ee 8 °M, Me8MM8 (8.8 e) eee eeeee eee eee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeee eee 88–88 eee. MeMMe ee MM8Me8 (88 eM) eee eeeee ee eee eeeeeee, eee, eeeee eeeeeeeeee ee eee eeeeee, eee eeeeeee eeeee eee eeeeeee eeeeeeeee eeee eee eeeeeee eeeeeee (8 × 88 eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee 8 M MMM. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee eee eeee eee eee eeeeee. Meee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee) ee eeeeee eee eeee eeee; eeeee: 88%.
Meeeee Meeeeeeee 8; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.
M eeee ee M8[MeM8(MM)8] (8.8 ee, 8.88 eeee), M8MM8 (888 ee, 8.8 eeee), M8[Me(MM)8] (888 ee, 8.8 eeee), MeM(MM)8 (888 ee, 8.8 eeee), eee eee eeeeeeee eeeeeeee eeeeee (8.88 eeee) ee e-MeMM/M8M (8:8; 88 eM) eee eeeeeee ee ee. Mee eeeeeeeee 8 (8.8 eeee) eee eeeee ee eee eeeeeee eee eee eeeee eee eeeeee eee eeeeeee eee 88 e ee ee. Me eeeeeee eeee ee Me8M8M8 eee eeeee eee eee eeeeeee eee eeeeeeeeeee eeeeeee MM8Me8 eee M8M. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeeeee ee eeee eee eeeee eeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeee eee eeeeeeeeeeee eeee eeeeeeee.
References
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